Ammonia → 5-(4-Methoxyphenyl)-7-(1-methylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 611524Notes

Reaction equation

Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:19]([CH3:21])[CH3:20])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:22]>O1CCOCC1>[NH2:22][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:19]([CH3:21])[CH3:20])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-7-isopropyl-5-(4-methoxyphenyl)pyrrolo-[2,3-d]pyrimidine (1.6 g), concentrated ammonia (80 ml, S.G. 0.880) and 1,4-dioxane (80 ml) was heated in a pressure vessel at 120° C. for 18 hours. The mixture was cooled to ambient temperature and the solvent was removed under reduced pressure to give a solid residue which was partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, dried, filtered and evaporated to give 4-amino-7-isopropyl-5-(4-methoxyphenyl)pyrrolo[2,3-d]-pyrimidine. The structure was confirmed by 1H nmr.

Workup

temperatureThe mixture was cooled to ambient temperature
customthe solvent was removed under reduced pressure
customto give a solid residue which
customwas partitioned between ethyl acetate (100 ml) and water (100 ml)
extractionThe aqueous layer was extracted with ethyl acetate
washthe combined organic layers were washed with water
customdried
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-f08c91fbda39413b92b0384fb5e6c2be
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06001839

Reaction notes

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