6-[(E)-2-(dimethylamino)vinyl]-5-nitropyrimidine-2,4-diol → 1,5-Dihydro-Pyrrolo(3,2-D)Pyrimidine-2,4-Dione
Reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[NH:10][C:9](=[O:11])[NH:8][C:7](=[O:12])[C:6]=1[N+:13]([O-])=O>C(O)(=O)C.[Zn]>[NH:10]1[C:5]2[CH:4]=[CH:3][NH:13][C:6]=2[C:7](=[O:12])[NH:8][C:9]1=[O:11]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 6-[(e)-2-(dimethylamino)vinyl]-5-nitropyrimidine-2,4(1H,3H)-dione (1.43 g, 6.36 mmol) in acetic acid (23 mL) was heated to 80° then zinc dust (2 g, 30.77 mmol) was added slowly over 1 h. The resulting suspension was heated for a further 1 h then allowed to cool to room temperature. The solid was collected by filtration then washed with acetic acid. The solid was transferred to a beaker and washed with water (25 mL), collected then dissolved in sodium hydroxide (5%, 10 mL). This solution was warmed to 70° and stirred for 30 min Acetic acid was added until pH 5-6 then the precipitate collected and washed with cold water then ethanol. The resultant solid was dried in vacuo to furnish 1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (0.62 g, 65%).
Workup
- temperaturewas heated to 80°
- temperatureThe resulting suspension was heated for a further 1 h
- filtrationThe solid was collected by filtration
- washthen washed with acetic acid
- washwashed with water (25 mL)
- customcollected
- dissolutionthen dissolved in sodium hydroxide (5%, 10 mL)
- temperatureThis solution was warmed to 70°
- additionwas added until pH 5-6
- customthe precipitate collected
- washwashed with cold water
- customThe resultant solid was dried in vacuo
Sources & evidence
- ORD record
- ord-76c237d682174b1bafa169957f165e45
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765755B2
Reaction notes
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