Chlorotrimethylsilane → HCID 44467885, compound

HRID 2381706Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:11][CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:29])[C:24]([CH:26]2[CH2:28][CH2:27]2)=[O:25])=[CH:19][CH:18]=1.C[Si](Cl)(C)C>C(O)CCC>[CH:12]1([NH:11][C:4]2[C:5]3[CH:10]=[CH:9][NH:8][C:6]=3[N:7]=[C:2]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]([CH3:29])[C:24]([CH:26]4[CH2:27][CH2:28]4)=[O:25])=[CH:21][CH:22]=3)[N:3]=2)[CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 115 °C

Procedure

To a suspension of 2-chloro-N-cyclobutyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (67 mg, 0.3 mmol) in nBuOH (0.8 mL) was added N-(4-aminophenyl)-N-methylcyclopropanecarboxamide (85 mg, 0.45 mmol) and TMSCl (0.02 mL, 0.15 mmol). After heating at 115° C. for 2 h, the mixture was cooled and purified by preparative HPLC to give N-(4-(4-(cyclobutylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylcyclopropanecarboxamide (7 mg). MS found for C21H24N6O as (M+H)+ 377.2. λ=208.7, 272.4, 304.5.

Workup

temperaturethe mixture was cooled
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-9da78ec9bea6411594a49ab4d75d3386
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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