1,2-Dichloroethane → 2-(Methylthio)-6-phenylpyrimidine-4-carboxamide

HRID 68298

Reaction equation

HRID 68298 reaction equation
C[N:2]1CCOCC1.[CH3:8][S:9][C:10]1[N:15]=[C:14]([C:16](O)=[O:17])[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:11]=1.[Cl-].[NH4+].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:8][S:9][C:10]1[N:15]=[C:14]([C:16]([NH2:2])=[O:17])[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:11]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 393492022-(Methylthio)-6-phenylpyrimidine-4-carboxylic acid

Product 1

HCID 588727612-(Methylthio)-6-phenylpyrimidine-4-carboxamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Methylmorpholine (2.31 mL, 21 mmol) was added dropwise by syringe to a mixture of 2-methylsulfanyl-6-phenylpyrimidine-4-carboxylic acid (3.45 g, 14 mmol), ammonium chloride (4.27 g, 80 mmol), HOBt (2.84 g, 21 mmol), and EDC (4.0 g, 21 mmol) in DMF (40 mL) at room temperature. The reaction solution was stirred at room temperature for 3 h before the DMF was removed by rotary evaporation. Column chromatography (SiO2, DCM/EtOAc 5:1) afforded 3.23 g of 2-(methylthio)-6-phenylpyrimidine-4-carboxamide as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.25 (m, 2H), 8.13 (s, 1H), 7.59 (m, 3H), 2.62 (s, 3H). HPLC ret. time 2.71 min, 10-100% CH3CN, 5 min gradient. ESI-MS m/z 246.1 (M+H)+.

Workup

  1. customwas removed by rotary evaporation

Sources & evidence

ORD record
ord-7f173a098f5a4026aa5fcce250a12d7a
Source dataset
uspto-grants-2014_09
Patent number
US08822451B2

Linked notes

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