2-Chloropyrimidine → HCID 131724173, compound

HRID 478422Notes

Reaction equation

HRID 478422 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[CH2:20][CH2:19][C@H:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C@H:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1>C(Cl)Cl>[F:34][C:2]([F:33])([F:1])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[CH2:20][CH2:19][C@H:18]([N:21]3[CH2:26][CH2:25][N:24]([C:36]4[N:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH2:23][CH2:22]3)[C@H:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 131724158HCID 131724158, compound

Product 1

HCID 131724173HCID 131724173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Rac-cis-(3,5-Bis-trifluoromethyl-phenyl)-(3-phenyl-4-piperazin-1-yl-piperidin-1-yl)-methanone (300 mg, 0.62 mmol) and 2-chloropyrimidine (71 mg, 0.68) were stirred at 100° C. overnight. The reaction mixture was taken up in 1 mL methylene chloride and chromatographed on silica gel with methylen chloride/methanol/triethyl amine 90:10:1. The desired product (181 mg, 47%) was a light yellow solid, MS: m/e=564.3 (M+H+).

Workup

  1. customchromatographed on silica gel with methylen chloride/methanol/triethyl amine 90:10:1

Sources & evidence

ORD record
ord-8fa0861b6081478c8f1cdce3bdd8f6bd
Source dataset
uspto-grants-2003_11
Patent number
US06642226B2

Reaction notes

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