Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → Carbamic acid, (1,4,5,6-tetrahydro-5-(3-methoxyphenyl)-2-pyrimidinyl)-, methyl ester

HRID 2059215Notes

Reaction equation

HRID 2059215 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:12][NH2:13])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH3:14][O:15][C:16]([NH:18][C:19](=NC(OC)=O)SC)=[O:17]>CO>[CH3:14][O:15][C:16]([NH:18][C:19]1[NH:11][CH2:10][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12][N:13]=1)=[O:17]

Participants

4

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 13034543HCID 13034543, compound

Product 1

HCID 54213Carbamic acid, (1,4,5,6-tetrahydro-5-(3-methoxyphenyl)-2-pyrimidinyl)-, methyl esterYield 68.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2.61 g (14.5 m. mole) of 2-(3-methoxyphenyl)-1,3-propanediamine in 200 ml of methanol is combined with a solution of 3.0 g (14.55 m. mole) of 1,3-bis(methoxycarbonyl)-S-methylisothiourea in 200 ml of methanol and allowed to stand at room temperature over night. The crystalline product which separates is collected, washed with methanol and dried at 78° under vacuum to give 2.62 g of 2-methoxycarbonylamino-5-(3-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine, mp 218°-221°.

Workup

  1. waitto stand at room temperature over night
  2. customThe crystalline product which separates is collected
  3. washwashed with methanol
  4. customdried at 78° under vacuum

Sources & evidence

ORD record
ord-502f0b69107f4f9cb847717fc7384166
Source dataset
uspto-grants-1982_03
Patent number
US04322421

Reaction notes

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