Chlorotrimethylsilane → HCID 57990283, compound

HRID 2281367Notes

Reaction equation

HRID 2281367 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:27][CH3:28])[C:5]2[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:29][C:30]1[CH:38]=[C:37]2[C:33]([CH:34]=[N:35][NH:36]2)=[CH:32][CH:31]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:36]1[C:37]2[C:33](=[CH:32][CH:31]=[C:30]([NH:29][C:2]3[N:3]=[C:4]([NH:27][CH3:28])[C:5]4[C:10]([C:11]5[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=5)=[CH:9][NH:8][C:6]=4[N:7]=3)[CH:38]=2)[CH:34]=[N:35]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 814231H-Indazol-6-amineHCID 57990430HCID 57990430, compound

Product 1

HCID 57990283HCID 57990283, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
115 °C

Procedure

To a mixture of 2-chloro-N-methyl-5-(pyridin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.075 g, 0.182 mmol) in nBuOH (1 mL) was added 6-aminoindazole (0.048 g, 0.36 mmol) and TMSCl (0.06 mL, 0.46 mmol). After heating at 115° C. for 72 h, the mixture was purified by preparative HPLC to give N2-(1H-indazol-6-yl)-N4-methyl-5-(pyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (0.03 g), MS (MH 357.2), λ=203.9, 246.3, 305.6.

Workup

  1. customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-eb575d588b0d4031adfa1f475d75a15d
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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