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

HRID 1509013ノート

反応式

HRID 1509013 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ef096ebacaf247bcbca6e2ae5c5a0aa6
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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