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

HRID 883551노트

반응식

HRID 883551 반응식
[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

참가 물질

5

반응물 3

HCID 7764Ethyl cyanoacetateHCID 2795339N-CyclopropylmethylthioureaHCID 10942334Sodium Methoxide

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bdf2d801adb4464f95b38e4ec1be0daf
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236951B2

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