(3,4,5-trifluorophenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound and/or its salt was prepared by a procedure similar to that described for E111 starting from (3,4,5-trifluorophenyl)methanol and tert-butyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidine-1-carboxylate.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of NaH (38.3 mg, 0.956 mmol) in DMF (2 mL) was added (3,4,5-trifluorophenyl)methanol (65 mg, 0.401 mmol) at rt. The reaction mixture was stirred for 5 mins at rt, and then 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one trifluoroacetic acid salt (100 mg, 0.319 mmol) was added. The reaction mixture was stirred for another 1 h at rt, quenched with water and then filtered to give clear solution. The solution was purified by MDAP (0.3% TFA in water/MeCN) to afford the title compound as its TFA salt (16 mg, 0.036 mmol, 11.42%). The reaction mixture was stirred for another 1 h at rt quenched with water filtered to give clear solution The solution was purified by MDAP (0.3% TFA in water/MeCN)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of NaH (38.3 mg, 0.956 mmol) in DMF (2 mL) was added (3,4,5-trifluorophenyl)methanol (65 mg, 0.401 mmol) at rt. The reaction mixture was stirred for 5 mins at rt, and then 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one trifluoroacetic acid salt (100 mg, 0.319 mmol) was added. The reaction mixture was stirred for another 1 h at rt, quenched with water and then filtered to give clear solution. The solution was purified by MDAP (0.3% TFA in water/MeCN) to afford the title compound as its TFA salt (16 mg, 0.036 mmol, 11.42%). The reaction mixture was stirred for another 1 h at rt quenched with water filtered to give clear solution The solution was purified by MDAP (0.3% TFA in water/MeCN)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification. was slowly added in portions over a period of 30 min The oily layer was extracted into CH2Cl2 (250 ml) the organic layer washed with water (200 ml) dried (MgSO4) evaporated