Cyclopentanecarboximidamide → 2-cyclopentyl-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

HRID 1509029ノート

反応式

HRID 1509029 の反応式
[CH:1]1([C:6](=[NH:8])[NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=[C:10]1[CH2:15][CH2:14][CH2:13][S:12][CH:11]1[C:16](OC)=[O:17].C[O-].[Na+]>C(O)C>[CH:1]1([C:6]2[N:8]=[C:16]([OH:17])[C:11]3[S:12][CH2:13][CH2:14][CH2:15][C:10]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 4452694CyclopentanecarboximidamideHCID 10942334Sodium MethoxideHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylate

生成物 1

HCID 1785174212-cyclopentyl-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one収率 44%

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 cyclopentanecarboximidamide (3.2 g, 28.0 mmol) in ethanol (150 mL) was added methyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate (4.95 g, 28.0 mmol) and sodium methoxide (1.5 g, 28.0 mmol). The mixture was stirred at 85° C. for 16 h. The ethanol was removed under vacuum and the residue was diluted with water and extracted with methylene chloride. The organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was diluted with hexanes and the solid was filtered to afford the title compound (2.9 g, 44%) as a white solid. MW=236.33. 1H NMR (CDCl3, 500 MHz) δ 11.41 (s, 1H), 3.13-2.99 (m, 1H), 2.99-2.94 (m, 2H), 2.81-2.70 (m, 2H), 2.21-2.14 (m, 2H), 2.14-2.04 (m, 2H), 1.92-1.79 (m, 4H), 1.73-1.64 (m, 2H); APCI MS m/z 237 [M+H]+.

後処理

  1. customThe ethanol was removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. additionThe residue was diluted with hexanes
  8. filtrationthe solid was filtered

出典と根拠

ORDレコード
ord-68d64a8e58a74c3680e26ba069de36b6
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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