Ethyl isothiocyanatoformate → Ethyl [(4,6-dimethoxypyrimidin-2-yl)amino]carbono thioylcarbamate

HRID 1058555Notes

Reaction equation

HRID 1058555 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH2:12]([O:14][C:15]([N:17]=[C:18]=[S:19])=[O:16])[CH3:13]>O1CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:18]([NH:17][C:15](=[O:16])[O:14][CH2:12][CH3:13])=[S:19])[N:7]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 1189462-Amino-4,6-dimethoxypyrimidine

Product 1

HCID 13607520Ethyl [(4,6-dimethoxypyrimidin-2-yl)amino]carbono thioylcarbamateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4,6-dimethoxypyrimidine (5.0 g, 36 mmol) was dissolved in dry tetrahydrofuran (THF, 35 mL), ethoxycarbonylisothiocyanate (6.4 mL, 54 mmol) was added and the solution was allowed to stir at room temperature. After 24 hours, the solvent is removed in vacuo and the residue was mixed with ether to form a crystalline solid. The solids were removed by vacuum filtration and dried to afford ethyl [(4,6-dimethoxypyrimidin-2-yl)amino]carbono thioylcarbamate as a tan solid (8.9 g, 87%). mp 196-197° C. 1H NMR (CDCl3): δ 13.2 (bs, 1H); 8.8 (bs, 1H); 5.80 (s, 1H); 4.32-4.25 (q, 2H, J=7.2); 3.93 (s, 3H); 1.30 (t, 3H, J=7.2).

Workup

  1. customthe solvent is removed in vacuo
  2. additionthe residue was mixed with ether
  3. customto form a crystalline solid
  4. customThe solids were removed by vacuum filtration
  5. customdried

Sources & evidence

ORD record
ord-de9a939e983b4b728f15584fe91e8536
Source dataset
uspto-grants-2003_02
Patent number
US06518222B2

Reaction notes

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