Potassium Carbonate → 4-Chloro-6-[N-(4,4,4-trifluorobutyl)-2-chloro-5-methylanilino]pyrimidine

HRID 987556Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[CH:4][N:3]=1.[F:17][C:18]([F:24])([F:23])[CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCC(C)C>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:21][CH2:20][CH2:19][C:18]([F:24])([F:23])[F:17])[C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Chloro-6-(2-chloro-5-methylanilino)pyrimidine (Reference Example 12) (0.28 g, 1.1 mmol) and 1,1,1-trifluoro-4-bromobutane (0.32 g, 1.67 mmol) were dissolved in NMP (2 ml). Anhydrous potassium carbonate (0.31 g, 2.2 mmol) was added and the mixture heated to 50° C. for three hours. Following an aqueous work-up the product was obtained by column chromatography on silica gel using EtOAc-isohexane mixtures. (0.3 g, 75%). M/z 364 (MH)+.

Workup

customwas obtained by column chromatography on silica gel

Sources & evidence

ORD record: ord-6c3abc9d8f7844c284714a36e889343f
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632820B1

Reaction notes

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