4-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidine → N-(2-t-butoxycarbonylaminophenyl)-4-{5-[2-(methylthio)pyrimidin-4-yl]thien-2-yl}benzamide

HRID 888043Notes

Reaction equation

HRID 888043 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].Br[C:34]1[S:38][C:37]([C:39]2[CH:44]=[CH:43][N:42]=[C:41]([S:45][CH3:46])[N:40]=2)=[CH:36][CH:35]=1>C(OCC)(=O)C.O>[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:18]=[CH:19][C:20]([C:34]2[S:38][C:37]([C:39]3[CH:44]=[CH:43][N:42]=[C:41]([S:45][CH3:46])[N:40]=3)=[CH:36][CH:35]=2)=[CH:21][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 28205344-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidineHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 68408076N-(2-t-butoxycarbonylaminophenyl)-4-{5-[2-(methylthio)pyrimidin-4-yl]thien-2-yl}benzamide

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

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, 219 mg, 0.5 mmol) was reacted with 4-(5-bromothien-2-yl)-2-(methylthio)pyrimidine (145 mg, 0.5 mmol). The crude residue stirred in ethyl acetate/water for 1 hour before being filtered, and the aqueous removed using a Varian Chem Elut Column (CE1010). The resulting solution was concentrated and recrystallised from methanol to give the title compound; Mass Spectrum: M+H+-Boc 463.

Workup

  1. filtrationbefore being filtered
  2. customthe aqueous removed
  3. concentrationThe resulting solution was concentrated
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-1894dd042f2441bc8f8753e2c3887135
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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