Water → 2-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 645671

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[N:28][NH:29]2)=[CH:25][CH:24]=1.C(N(CC)CC)C.O>C(O)CCC.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[N:28][NH:29]3)=[CH:25][CH:24]=2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (400 mg, 1.17 mmol), 6-aminoindazole (171 mg, 1.29 mmol) and triethylamine (0.400 mL, 2.88 mmol) in n-butyl alcohol (10 mL) was heated at 80° C. overnight. After cooling down, H2O and CH2Cl2 were added. The organic phase was separated, washed with 1N HCl, followed by 5% NaHCO3, before it was dried over Na2SO4 and concentrated in vacuo to give 2-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine as a solid (490 mg).

Workup

temperatureAfter cooling down
customThe organic phase was separated
washwashed with 1N HCl
dry with materialwas dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3d71c9c56c3a49abbe358121e17d38b5
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Linked notes

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