2,4-Dichloropyrimidine → 2-Chloro-4-(4-nitrophenyl)pyrimidine

HRID 1771536Notes

Reaction equation

HRID 1771536 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)O1.[Cl:41][C:42]1[N:47]=[C:46](Cl)[CH:45]=[CH:44][N:43]=1>>[Cl:41][C:42]1[N:47]=[C:46]([C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)[CH:45]=[CH:44][N:43]=1

Participants

4

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholine

Product 1

HCID 110536262-Chloro-4-(4-nitrophenyl)pyrimidineYield 53%

Procedure

Method as described for intermediate 5 using 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane and 2,4-dichloropyrimidine. The mixture was purified using flash chromatography (0-100% EtOAc in petroleum ether 40-60) to afford the title compound (1.45 g, 53%)

Workup

  1. customThe mixture was purified

Sources & evidence

ORD record
ord-85260b03c09a4b86b8db868ddf1cd12f
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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