1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion

To a stirred slurry of (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidin-2, 4-dioneA suspension of 6-[(e)-2-(dimethylamino)vinyl]-5-nitropyrimidine- 2, 4(1 H, 3H)-dione (1.43g, 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 (5percent, 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 lH-pyrrolo[3, 2-d]pyrimidine- 2, 4(3H, 5H)-dione (0.62 g, 65percent).[00473] To a stirred solution of ethyl3-ureido-1H-pyrrole-2-carboxylate (26.2 mmol) in H20 (95 mL) wasadded NaOH (6 g). After stirred at refluxing for 30 min, the reaction mixture was cooled down to roomtemperature and acidified to pH~ 6 by cone. HCl, the brown solid was collected by filtration to provide 1, 5-dihydro-2H-pyrrolo[3, 2-d]pyrimidine-2, 4(3H)-dione (1.8 g, 45percent over 2 steps) which was used in the nextstep without purification. LC-MS (ESI): m/z (M+1) 152.02

Used for the preparation of pyrazolopyrimidine derivatives or analogs thereof as CCR4 function modulators.

Molecular Weight:151.12
XLogP3:-0.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Exact Mass:151.038176411
Monoisotopic Mass:151.038176411
Topological Polar Surface Area:74
Heavy Atom Count:11
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes