2,4-Dichloropyrimidine → N-(2-t-butoxycarbonylaminophenyl)-4-(2-chloropyrimidin-4-yl)benzamide

HRID 888035Notes

Reaction equation

HRID 888035 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:33][C:34]1[N:39]=[C:38](Cl)[CH:37]=[CH:36][N:35]=1>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20]([C:36]2[CH:37]=[CH:38][N:39]=[C:34]([Cl:33])[N:35]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 86599911N-(2-t-butoxycarbonylaminophenyl)-4-(2-chloropyrimidin-4-yl)benzamideYield 32%

Procedure

Using an analogous procedure to that described in Method 4, N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13, 3.9 g, 8.9 mmol) was reacted with 2,4-dichloropyrimidine (3.06 g, 20.5 mmol). The crude residue was purified by flash chromatography on silica, eluting with ethyl acetate/isohexane (1:1) to give the title compound (1.2 g, 32%); NMR Spectrum: (DMSO-d6) 1.45 (s, 9H), 7.23 (m, 2H), 7.57 (t, 2H), 8.15 (d, 2H), 8.29 (d, 1H), 8.38 (d, 2H), 8.73 (s, 1H), 8.91 (d, 1H), 10.00 (s, 1H); Mass Spectrum: M−H− 423.

Workup

  1. customThe crude residue was purified by flash chromatography on silica
  2. washeluting with ethyl acetate/isohexane (1:1)

Sources & evidence

ORD record
ord-f0240b6ff9df4fc39f0657413cb1211e
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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