phenyl N-propan-2-ylcarbamate

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

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

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

Procedure: Sodium hydride (48 mg, 1.2 mmol) was suspended in N,N-dimethylformamide (2.5 ml); 6-amino-4-(1H-5-indolylamino)pyrimidine (225.3 mg, 1.0 mmol) was added thereto at room temperature under nitrogen stream; the reaction mixture was stirred for 30 minutes; phenyl N-(2-propyl)carbamate (215 mg, 1.2 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluent; ethyl acetate); eluted fractions were concentrated; ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, and dried under aeration to yield the title compound (31.3 mg, 0.079 mmol, 7.9%) as white crystals. at room temperature and the reaction mixture was stirred overnight The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and the organic layer was washed with water and brine dried over anhydrous sodium sulfate After the solvent was distilled off the residue was purified by silica gel column chromatography (eluent; ethyl acetate) eluted fractions were concentrated ethyl acetate was added to the residue to crystallize and the crystals were filtered off dried under aeration

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

Procedure: Sodium hydride (48 mg, 1.2 mmol) was suspended in N,N-dimethylformamide (2.5 ml); 6-amino-4-(1H-5-indolylamino)pyrimidine (225.3 mg, 1.0 mmol) was added thereto at room temperature under nitrogen stream; the reaction mixture was stirred for 30 minutes; phenyl N-(2-propyl)carbamate (215 mg, 1.2 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluent; ethyl acetate); eluted fractions were concentrated; ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, and dried under aeration to yield the title compound (31.3 mg, 0.079 mmol, 7.9%) as white crystals. at room temperature and the reaction mixture was stirred overnight The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and the organic layer was washed with water and brine dried over anhydrous sodium sulfate After the solvent was distilled off the residue was purified by silica gel column chromatography (eluent; ethyl acetate) eluted fractions were concentrated ethyl acetate was added to the residue to crystallize and the crystals were filtered off dried under aeration

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

Procedure: Sodium hydride (48 mg, 1.2 mmol) was suspended in N,N-dimethylformamide (2.5 ml); 6-amino-4-(1H-5-indolylamino)pyrimidine (225.3 mg, 1.0 mmol) was added thereto at room temperature under nitrogen stream; the reaction mixture was stirred for 30 minutes; phenyl N-(2-propyl)carbamate (215 mg, 1.2 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluent; ethyl acetate); eluted fractions were concentrated; ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, and dried under aeration to yield the title compound (31.3 mg, 0.079 mmol, 7.9%) as white crystals. at room temperature and the reaction mixture was stirred overnight The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and the organic layer was washed with water and brine dried over anhydrous sodium sulfate After the solvent was distilled off the residue was purified by silica gel column chromatography (eluent; ethyl acetate) eluted fractions were concentrated ethyl acetate was added to the residue to crystallize and the crystals were filtered off dried under aeration

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

Procedure: Using the same procedure as in Example 4, isopropylamine (2.36g, 0.04 mole) was reacted with phenyl chloroformate (6.0g, 0.038 mole) in methylene chloride (35 ml) and with aqueous sodium hydroxide. The reaction mixture was stirred for two hours, then allowed to separate. The organic layer was dried over anhydrous magnesium sulfate, then gravity filtered. The filtrate was stripped of solvent on the Rotovap, leaving pure white crystals weighing 6.66g, MP 81°-82° C. to separate The organic layer was dried over anhydrous magnesium sulfate gravity filtered leaving pure white crystals