2-(Methylthio)-1H-pyrimidin-4-one → 2-(3-(2-methylthiazol-4-yl)phenylamino)pyrimidin-4(3H)-one

HRID 1692993Notes

Reaction equation

HRID 1692993 reaction equation
CS[C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[CH3:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[N:15]=1>COCCOCCOC>[CH3:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:17]=[C:18]([NH:22][C:3]3[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=3)[CH:19]=[CH:20][CH:21]=2)[N:15]=1

Participants

4

Reactant 2

HCID 798232-(Methylthio)-1H-pyrimidin-4-oneHCID 7365353-(2-Methyl-thiazol-4-yl)-phenylamine

Product 1

HCID 577809112-(3-(2-methylthiazol-4-yl)phenylamino)pyrimidin-4(3H)-oneYield 25%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

To 2-(methyl-thio)pyrimidine-4(3H)-one, 1, (1 g, 14.08 mmol) in diglyme (9 mL) is added 3-(2-methylthiazol-4-yl)benzenamine (3.20 g, 16.90 mmol). The resulting mixture is heated to reflux and stirred for 18 hours. A solid forms upon cooling the mixture to room temperature. The solid is washed with hexanes to afford 1.0 g (25% yield) of the desired compound. MS (ESI, pos. ion) m/z: 285 (M+1).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux
  3. washThe solid is washed with hexanes

Sources & evidence

ORD record
ord-522812e860dc4d1ebf26a57a44ee5a9b
Source dataset
uspto-grants-2012_04
Patent number
US08158641B2

Reaction notes

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