Water → 2-chloro-N-(3-aminosulfonyl-phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2381679Notes

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:24]=[C:25]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.C(N(CC)CC)C.O>C(O)CCC.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([NH2:32])(=[O:30])=[O:31])[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 (200 mg, 0.58 mmol), 3-aminobenzenesulfonamide (111 mg, 0.65 mmol) and triethylamine (0.200 mL, 1.44 mmol) in nBuOH (6 mL) was heated at 80° C. overnight. The mixture was then heated at 110° C. for another 24 h. After cooling down, H2O and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, and it was dried over Na2SO4, concentrated in vacuo to give 2-chloro-N-(3-aminosulfonyl-phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine as a solid (210 mg).

Workup

temperatureThe mixture was then heated at 110° C. for another 24 h
temperatureAfter cooling down
customThe organic phase was separated
washwashed with 1N HCl
dry with materialwith 5% NaHCO3, and it was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-657a70f080034eacab9775c3aba176df
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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