3-Chloro-benzamidine → 2-(3-chlorophenyl)-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

HRID 1509013노트

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HRID 1509013 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].O=[C:12]1[CH2:17][CH2:16][CH2:15][S:14][CH:13]1[C:18](OC)=[O:19].C[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:18]([OH:19])[C:13]3[S:14][CH2:15][CH2:16][CH2:17][C:12]=3[N:7]=2)[CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 2041443-Chloro-benzamidineHCID 10942334Sodium MethoxideHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylate

생성물 1

HCID 1785174692-(3-chlorophenyl)-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one수율 67.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

To a solution of 3-chlorobenzimidamide (4.3 g, 27.7 mmol) in ethanol (120 mL) was added methyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate (4.82 g, 27.7 mmol) and sodium methoxide (1.8 g, 33.2 mmol). The mixture was stirred at 85° C. for 16 h. After this time, the mixture was concentrated after which ethanol (10 mL) was added and the suspension was chilled to 0° C. HCl (2 M, 50 mL) was added and the suspension was filtered and washed with water. The solid was dried under heat and vacuum to afford the title compound (5.2 g, 67%) as a light yellow solid. MW=278.75. 1H NMR (DMSO-d6, 500 MHz) δ 12.81 (s, 1H), 8.12 (s, 1H), 8.03 (d, J=7.5 Hz, 1H), 7.63-7.58 (m, 1H), 7.56-7.51 (m, 1H), 3.01-2.95 (m, 2H), 2.74 (t, J=6.0 Hz, 2H), 2.12-2.04 (m, 2H); APCI MS m/z 279 [M+H]+.

후처리

  1. concentrationAfter this time, the mixture was concentrated after which ethanol (10 mL)
  2. additionwas added
  3. temperaturethe suspension was chilled to 0° C
  4. additionHCl (2 M, 50 mL) was added
  5. filtrationthe suspension was filtered
  6. washwashed with water
  7. customThe solid was dried
  8. temperatureunder heat

출처 및 근거

ORD 기록
ord-ef096ebacaf247bcbca6e2ae5c5a0aa6
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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