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

HRID 215740

Reaction equation

N[N:2]1[C:7](=[O:8])[C:6]2[S:9][CH:10]=[CH:11][C:5]=2[NH:4][C:3]1=[O:12].N([O-])=O.[Na+]>C(O)(=O)C.O>[NH:4]1[C:5]2[CH:11]=[CH:10][S:9][C:6]=2[C:7](=[O:8])[NH:2][C:3]1=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-amino-1H-thieno[3,2-d]pyrimidine-2,4-dione (1.70 g, 9.3 mmol) in a 1:1 mixture of acetic acid/H2O (155 mL) was added sodium nitrite (1.92 g, 27.8 mmol) portion-wise. The reaction mixture was heated to 60° C. until the evolution of brown gas ceased (2 h). Acetic acid was removed under reduced pressure and the solution was cooled to 0° C. The resulting white solid was collected by filtration to afford 0.77 g of the desired product. MS: 167.3. 1H NMR (400 MHz, d6-N,N-dimethylsulfoxide (d6-DMSO)) δ ppm 11.40 (br s, 1H), 8.04 (d, J=5.2 Hz, 1H), 6.91 (d, J=5.3 Hz, 1H), 3.34 (br s, 1H).

Workup

custom(2 h)
customAcetic acid was removed under reduced pressure
temperaturethe solution was cooled to 0° C
filtrationThe resulting white solid was collected by filtration

Sources & evidence

ORD record: ord-8ab6e7187008492b843effe1877e865e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193178B2

Linked notes

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