HCID 58315415, compound → HCID 178455434, compound

HRID 2359539Notes

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

Reactant 2

HCID 58315415HCID 58315415, compound

HCID 178455437HCID 178455437, compound

Product 1

HCID 178455434HCID 178455434, compoundYield 66%

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-cae3da0728044b17910d0c4f78f9eab6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685980B2

Reaction notes

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