Chlorotrimethylsilane → 2-(1H-indazol-6-ylamino)-4-(cyclopropylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

HRID 2281406Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:23][CH:24]2[CH2:26][CH2:25]2)[C:5]2[C:10]([C:11]#[N:12])=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:27][C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[N:33][NH:34]2)=[CH:30][CH:29]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:34]1[C:35]2[C:31](=[CH:30][CH:29]=[C:28]([NH:27][C:2]3[N:3]=[C:4]([NH:23][CH:24]4[CH2:25][CH2:26]4)[C:5]4[C:10]([C:11]#[N:12])=[CH:9][NH:8][C:6]=4[N:7]=3)[CH:36]=2)[CH:32]=[N:33]1

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of 2-chloro-4-(cyclopropylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (109 mg, 0.28 mmol), 6-aminoindazole (75 mg, 0.56 mmol) and TMSCl (0.089 mL, 0.70 mmol) in nBuOH (4 mL) was stirred at 116° C. for 18 h. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (6 mg). MS 331.1 (M+H); UV 246.2, 307.9 nm.

Workup

concentrationIt was then concentrated in vacuo
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-c8ce37453c0f45efb505d3f092f464f9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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