Chlorotrimethylsilane → N-(4-(4-(5-aminopentylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

HRID 2281448Notes

Reaction equation

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

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of N-(5-aminopentyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine (79 mg, 0.31 mmol), N-(4-aminophenyl)-N-methylacetamide (100 mg, 0.61 mmol) and trimethylsilyl chloride (0.150 mL, 1.19 mmol) in nBuOH (2 mL) was heated at 116° C. for 4 h. The mixture was then purified by HPLC to give the titled compound (9 mg). MS 382.2 (M+H); UV 210.8, 267.5, 305.5 nm.

Workup

customThe mixture was then purified by HPLC

Sources & evidence

ORD record: ord-9c5aee1387e249a3a9036560a86e991d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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