Ethyl cyanoacetate → 6-Amino-1-cyclopropylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

HRID 31063ノート

反応式

HRID 31063 の反応式
[CH:1]1([CH2:4][NH:5][C:6]([NH2:8])=[S:7])[CH2:3][CH2:2]1.C[O-].[Na+].[C:12]([CH2:14][C:15](OCC)=[O:16])#[N:13]>C(O)C>[NH2:13][C:12]1[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6](=[S:7])[NH:8][C:15](=[O:16])[CH:14]=1

参加物

5

反応物 3

HCID 7764Ethyl cyanoacetateHCID 2795339N-CyclopropylmethylthioureaHCID 10942334Sodium Methoxide

生成物 1

HCID 866010556-Amino-1-cyclopropylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one収率 56.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To 1-cyclopropylmethyl-2-thiourea (0.60 g, 4.6 mmol) in ethanol (10 mL) was added sodium methoxide (0.26 g, 4.8 mmol) and, after 5 minutes, ethyl cyanoacetate (0.50 mL, 4.6 mmol). The resulting mixture was heated to reflux for 2 h and 40 minutes followed by evaporation of the solvent under reduced pressure and treatment of the resulting yellow solid with 2M aqueous acetic acid (10 mL) giving a white solid. The solid was collected by filtration and washed with 2M aqueous acetic acid (10 mL), stirred with ethanol (10 mL) followed by evaporation and drying under reduced pressure, giving the title compound (0.51 g, 56%).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h and 40 minutes
  3. customfollowed by evaporation of the solvent under reduced pressure and treatment of the resulting yellow solid with 2M aqueous acetic acid (10 mL)
  4. customgiving a white solid
  5. filtrationThe solid was collected by filtration
  6. washwashed with 2M aqueous acetic acid (10 mL)
  7. customfollowed by evaporation
  8. customdrying under reduced pressure

出典と根拠

ORDレコード
ord-2e78d71160104c28a4a102b782dcc95d
出典データセット
uspto-grants-2008_09
特許番号
US07425560B2

反応ノート

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