Chlorotrimethylsilane → 5-bromo-N4-cyclobutyl-N2-(1H-indazol-6-yl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 2381650Notes

Reaction equation

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

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of 5-bromo-2-chloro-N-cyclobutyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (64 mg, 0.21 mmol), 6-aminoindazole (56 mg, 0.42 mmol) and TMSCl (0.050 mL, 0.40 mmol) in nBuOH (2 mL) was stirred at 116° C. for 4 h. It was then concentrated in vacuo. The residue was purified by HPLC to give a sample, which was further purified by preparative TLC using CH2Cl2/MeOH (95/5) as developing solvents to give the titled compound (1 mg). MS 398.3, 400.3 (M+H, Br pattern); UV 203.8, 247.4, 309.1 nm.

Workup

concentrationIt was then concentrated in vacuo
customThe residue was purified by HPLC
customto give a sample, which
customwas further purified by preparative TLC

Sources & evidence

ORD record: ord-a3f6d1ee73e8463488f54b4a3bd8508e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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