Urea → Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dione

HRID 2272932Notes

Reaction equation

HRID 2272932 reaction equation
CO[C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[NH2:11][C:12](N)=[O:13]>O>[NH:10]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3](=[O:4])[NH:11][C:12]1=[O:13]

Participants

4

Reactant 2

HCID 1176UreaHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 7059273Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A solid mixture of methyl-3-aminothiophene-2-carboxylate (76 g, 480 mmol) and urea (189 g, 3140 mmol) was heated, with stirring, to 180° C. for 5 h. The mixture was cooled to 90° C. and water (1000 ml) added. After stirring at room temperature for 16 h, a cream coloured solid was filtered and washed twice with further water. The solid was dried in vacuo at 40° C. to give the title compound in 94% yield, >95% purity. LC-MS m/z=169.0 [M+H]+; RT=1.29 min; LC-MS method 2. 1H NMR: δH (400 MHz, D6-DMSO) 6.90 (1H, d, J=5.5 Hz), 8.04 (1H, d, J=5.5 Hz), 11.10-11.80 (2H, b).

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled to 90° C.
  3. stirringAfter stirring at room temperature for 16 h
  4. filtrationwas filtered
  5. washwashed twice with further water
  6. customThe solid was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-f9c9f8b1875f41bc957852b1cd1e27ff
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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