2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile → HCID 178455434, compound
Reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]#[N:12])[N:8]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[N:7]=1.[C:18]([SiH2:22][O:23][C:24]([CH3:33])([CH3:32])[C:25]1[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=1)([CH3:21])([CH3:20])[CH3:19]>>[C:18]([SiH2:22][O:23][C:24]([CH3:33])([CH3:32])[C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:2]2[N:3]=[CH:4][C:5]3[CH:10]=[C:9]([C:11]#[N:12])[N:8]([CH:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)[C:6]=3[N:7]=2)=[N:29][CH:30]=1)([CH3:21])([CH3:19])[CH3:20]Participants
3
Procedure
Following Buchwald Procedure A, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile (95 mg, 0.385 mmol) and 5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamine (101 mg, 0.424 mmol) (Example C) gave 114 mg of 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamino]-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile [following SiO2 chromatography eluting with 1-2% MeOH/dichloromethane and subsequent trituration with diethyl ether].
Sources & evidence
- ORD record
- ord-b9a8b573ff7a47e19049f8b02333f80f