Hydrazine hydrate (1:1) → 3-Aminothieno[3,2-D]pyrimidine-2,4(1H,3H)-dione

HRID 215739Notes

Reaction equation

HRID 215739 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11]([O:13]CC)=O)=O.O.[NH2:17][NH2:18]>CCO>[NH2:17][N:18]1[C:3](=[O:2])[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[NH:10][C:11]1=[O:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 840181Methyl 3-((ethoxycarbonyl)amino)thiophene-2-carboxylate

Product 1

HCID 675407773-Aminothieno[3,2-D]pyrimidine-2,4(1H,3H)-dioneYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-ethoxycarbonylamino-thiophene-2-carboxylic acid methyl ester (3.43 g, 15.0 mmol) in EtOH (100 mL) was added hydrazine monohydrate (7.98 mL, 164.6 mmol). After heating at 90° C. for 12 h, the mixture was filtered to afford a fine yellow powder (1.70 g), which was used in the next step without further purification. MS: 184.2. 1H NMR (400 MHz, CD3OD) δ ppm 7.93 (d, J=5.3 Hz, 1H), 6.95 (d, J=5.3 Hz, 1H).

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-0425c03deb5f4dd6ad98357a06e309f6
Source dataset
uspto-grants-2012_06
Patent number
US08193178B2

Reaction notes

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