Dimethylformamide → 7-isobutyryl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51506Notes

Reaction equation

[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[O:7]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:28]3[C:27]([NH2:29])=[N:26][CH:25]=[N:24][C:23]=3[NH:22][CH:21]=2)=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C=O>N1C=CC=CC=1>[C:1]([N:22]1[C:23]2[N:24]=[CH:25][N:26]=[C:27]([NH2:29])[C:28]=2[C:20]([C:17]2[CH:16]=[CH:15][C:14]([O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:19][CH:18]=2)=[CH:21]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 20 °C

Procedure

Isobutyryl chloride (1.8 g) was added dropwise to a mixture of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (4.32 g), dry dimethyl-formamide (200 ml) and dry pyridine (2 ml) with stirring under nitrogen at 20° C. The mixture was stirred at ambient temperature for 1 hour and evaporated under vacuum. The residue was partitioned between water and ethyl acetate. The ethyl acetate was separated, dried and evaporated and the residue obtained was recrystallised from toluene to give 7-isobutyryl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 160.5-161° C.

Workup

stirringThe mixture was stirred at ambient temperature for 1 hour
customevaporated under vacuum
customThe residue was partitioned between water and ethyl acetate
customThe ethyl acetate was separated
customdried
customevaporated
customthe residue obtained
customwas recrystallised from toluene

Sources & evidence

ORD record: ord-b977410907254daabd8a9c7bcaa27135
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Reaction notes

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