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

반응식

[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.[NH2:11][C:12](N)=[O:13]>>[NH:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:9])[NH:11][C:12]1=[O:13]

참가 물질

반응물 2

HCID 1176Urea

HCID 89652Methyl 3-amino-2-thiophenecarboxylate

생성물 1

HCID 7059273Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dione

반응 조건

온도: 190 °C

실험 절차

A mixture of methyl 3-amino-2-thiophenecarboxylate 1 (13.48 g, 85.85 mmol) and urea (29.75 g, 5 eq.) was heated at 190° C. for 2 hours. The hot reaction mixture was poured onto sodium hydroxide solution and any insoluble material was removed by filtration. The mixture was then acidified (HCl, 2N) to yield 1H-thieno[3,2-d]pyrimidine-2,4-dione 2 as a white precipitate, which was collected by filtration and air dried (9.49 g, 66%). 1H NMR 400 MHz, d6-DMSO) 6.90 (1H, d, J=5.2 Hz), 8.10 (1H, d, J=5.2 Hz), 11.60-11.10 (2H, br s).

후처리

additionThe hot reaction mixture was poured onto sodium hydroxide solution
customany insoluble material was removed by filtration

출처 및 근거

ORD 기록: ord-02a3a77379f2477288045e7e2bef1df5
출처 데이터셋: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08536161B2

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