Sodium hydride → 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-butyrolactone

HRID 51496

Reaction equation

[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].Br[CH:27]1[CH2:32][CH2:31][O:30][C:28]1=[O:29]>CN(C)C=O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][N:8]([CH:27]3[CH2:32][CH2:31][O:30][C:28]3=[O:29])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (1.0 g) was added to a mixture of sodium hydride (0.158 g of a 60% dispersion in mineral oil) in dimethyl formamide (70 ml) with stirring under nitrogen at 0° C. The mixture was stirred at 0° C. for 1 hour and then α-bromo-γ-butyrolactone (0.60 g) in dimethylformamide (6 ml) was added dropwise with stirring at 0° C. The mixture was stirred at ambient temperature for 18 hours and then quenched with water (100 ml). The mixture was extracted with ethyl acetate. The combined extracts were dried and evaporated to give 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-butyrolactone as an oil which was used directly in b).

Workup

stirringThe mixture was stirred at 0° C. for 1 hour
stirringwith stirring at 0° C
stirringThe mixture was stirred at ambient temperature for 18 hours
customquenched with water (100 ml)
extractionThe mixture was extracted with ethyl acetate
customThe combined extracts were dried
customevaporated

Sources & evidence

ORD record: ord-6f66962956a94b1cb544567f732d7e9e
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Linked notes

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