2,4-Dichloropyrimidine → 2-Chloro-4-[(S)-3-(2-chloro-benzenesulfonyl)-pyrrolidin-1-yl]-pyrimidine

HRID 38043Notes

Reaction equation

OC(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([C@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1)(=[O:17])=[O:16].[Cl:23][C:24]1[N:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1.[F-].[K+]>C(#N)C>[Cl:23][C:24]1[N:29]=[C:28]([N:20]2[CH2:21][CH2:22][C@H:18]([S:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[Cl:8])(=[O:16])=[O:17])[CH2:19]2)[CH:27]=[CH:26][N:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

(S)-3-(2-Chloro-benzenesulfonyl)-pyrrolidine TFA salt (250 mg) was dissolved in ACN (3.0 mL). 2,4-Dichloropyrimidine (155 mg), TEA (0.39 mL) and KF (4 mg) were added to the solution. The reaction mixture was stirred at 150° C. in the microwave oven for 2 h. The reaction mixture was evaporated to dryness and purified with preparative HPLC to yield 2-Chloro-4-[(S)-3-(2-chloro-benzenesulfonyl)-pyrrolidin-1-yl]-pyrimidine (91 mg, 36%) as a light yellow solid. MS: m/z=358.0 [M+H]+.

Workup

customThe reaction mixture was evaporated to dryness
custompurified with preparative HPLC

Sources & evidence

ORD record: ord-2ca0e86aa85242c88ea12963c5459fad
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524710B2

Reaction notes

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