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

HRID 2281446Notes

Reaction equation

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

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of N-(2-aminoethyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine (71 mg, 0.34 mmol), N-(4-aminophenyl)-N-methylacetamide (110 mg, 0.67 mmol) and trimethylsilyl chloride (0.085 mL, 0.67 mmol) in nBuOH (2 mL) was heated at 116° C. for 3 h. More trimethylsilyl chloride (0.100 mL, 0.79 mmol) was added. After being stirred at 116° C. for another 2 h, the mixture was purified by HPLC to give the titled compound (28 mg). MS 340.2 (M+H); UV 201.4, 262.7, 303.1 nm.

Workup

customthe mixture was purified by HPLC

Sources & evidence

ORD record: ord-85d91752eb15422d827ed1d56b73d441
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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