3,3-dimethyl-2,4-dihydro-1H-isoquinoline

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

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

Procedure: In close analogy to the procedure described in Example 1, 6-chloro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 3,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield.

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

Procedure: In close analogy to the procedure described in Example 1, 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 3,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield.

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

Procedure: In close analogy to the procedure described in Example 1, 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 3,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield.

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

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

Procedure: To a stirred solution of naphthalene (5.8 g, 0.045 mol) in dimethoxyethane (50 mL) was added sodium metal (1.09 g, 0.039 mol.). The mixture was allowed to stir for four (4) hours until a dark green color persisted. To this was added of N-toluenesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (5.0 g, 0.016 mol.) in 20 mL of dimethoxymethane. The reaction was monitored by gas chromatography. When the reaction was complete (≈2 hours), the mixture was quenched with saturated sodium chloride (70 mL). The mixture was partitioned between ethyl acetate (250 mL) and 10% HCL (250 mL) and the organic layer was discarded. 10% Sodium hydroxide was added to the aqueous layer until a pH=7 was obtained. The aqueous layer was further extracted over methylene chloride (2×100 mL), dried over magnesium sulfate, filtered and concentrated (25° C./150 torr) to produce 2.2 g (86%) of 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline. (≈2 hours) the mixture was quenched with saturated sodium chloride (70 mL) The mixture was partitioned between ethyl acetate (250 mL) and 10% HCL (250 mL) 10% Sodium hydroxide was added to the aqueous layer until a pH=7 was obtained The aqueous layer was further extracted over methylene chloride (2×100 mL) dried over magnesium sulfate filtered concentrated (25° C./150 torr)

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

Procedure: To a stirred solution of naphthalene (5.8 g, 0.045 mol) in dimethoxyethane (50 mL) was added sodium metal (1.09 g, 0.039 mol.). The mixture was allowed to stir for four (4) hours until a dark green color persisted. To this was added of N-toluenesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (5.0 g, 0.016 mol.) in 20 mL of dimethoxymethane. The reaction was monitored by gas chromatography. When the reaction was complete (≈2 hours), the mixture was quenched with saturated sodium chloride (70 mL). The mixture was partitioned between ethyl acetate (250 mL) and 10% HCL (250 mL) and the organic layer was discarded. 10% Sodium hydroxide was added to the aqueous layer until a pH=7 was obtained. The aqueous layer was further extracted over methylene chloride (2×100 mL), dried over magnesium sulfate, filtered and concentrated (25° C./150 torr) to produce 2.2 g (86%) of 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline. (≈2 hours) the mixture was quenched with saturated sodium chloride (70 mL) The mixture was partitioned between ethyl acetate (250 mL) and 10% HCL (250 mL) 10% Sodium hydroxide was added to the aqueous layer until a pH=7 was obtained The aqueous layer was further extracted over methylene chloride (2×100 mL) dried over magnesium sulfate filtered concentrated (25° C./150 torr)

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

Procedure: To a stirred solution of naphthalene (5.8 g, 0.045 mol) in dimethoxyethane (50 mL) was added sodium metal (1.09 g, 0.039 mol.). The mixture was allowed to stir for four (4) hours until a dark green color persisted. To this was added of N-toluenesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (5.0 g, 0.016 mol.) in 20 mL of dimethoxymethane. The reaction was monitored by gas chromatography. When the reaction was complete (≈2 hours), the mixture was quenched with saturated sodium chloride (70 mL). The mixture was partitioned between ethyl acetate (250 mL) and 10% HCL (250 mL) and the organic layer was discarded. 10% Sodium hydroxide was added to the aqueous layer until a pH=7 was obtained. The aqueous layer was further extracted over methylene chloride (2×100 mL), dried over magnesium sulfate, filtered and concentrated (25° C./150 torr) to produce 2.2 g (86%) of 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline. (≈2 hours) the mixture was quenched with saturated sodium chloride (70 mL) The mixture was partitioned between ethyl acetate (250 mL) and 10% HCL (250 mL) 10% Sodium hydroxide was added to the aqueous layer until a pH=7 was obtained The aqueous layer was further extracted over methylene chloride (2×100 mL) dried over magnesium sulfate filtered concentrated (25° C./150 torr)

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

Procedure: In close analogy to the procedure described in Example 1, 6-chloro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 3,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield.

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

Procedure: In close analogy to the procedure described in Example 1, 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 3,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield.