Methanol → 2-(3-chlorophenyl)-6-cyclopropylpyrimidin-4(3H)-one

HRID 1508910노트

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HRID 1508910 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].[CH:11]1([C:14](=O)[CH2:15][C:16](OCC)=[O:17])[CH2:13][CH2:12]1.C[O-].[Na+].CO>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:16](=[O:17])[CH:15]=[C:14]([CH:11]3[CH2:13][CH2:12]3)[N:7]=2)[CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 2041443-Chloro-benzamidineHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 10942334Sodium Methoxide

생성물 1

HCID 1359755402-(3-chlorophenyl)-6-cyclopropylpyrimidin-4(3H)-one수율 33.1%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

A 500-mL round bottomed flask was charged with 3-chlorobenzimidamide (5.75 g, 30.1 mmol), ethyl 3-cyclopropyl-3-oxopropanoate (5.00 g, 32.0 mmol), and ethanol (100 mL) and the mixture cooled to 0° C. To the stirred mixture was added 25% sodium methoxide in methanol (15.0 mL, 64.0 mmol). The resulting mixture was stirred at reflux for 20 h. After cooling to room temperature, the mixture was evaporated under reduced pressure to 25 mL. The residual slurry was cautiously treated with 2N HCl (50 mL) forming a solid. The solid was collected by filtration and washed with water followed by ether to afford the title compound (2.46 g, 31%) as a white solid, which was carried forward into the next step without further purification. MW=246.69. 1H NMR (DMSO-d6, 500 MHz) δ 12.55 (s, 1H), 8.13 (s, 1H), 8.06 (d, J=7.5 Hz, 1H), 7.64-7.60 (m, 1H), 7.54 (t, J=8.0 Hz, 1H), 6.34 (s, 1H), 2.00-1.93 (m, 1H), 1.08-1.02 (m, 2H), 0.99-0.91 (m, 2H).

후처리

  1. temperatureat reflux for 20 h
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was evaporated under reduced pressure to 25 mL
  4. additionThe residual slurry was cautiously treated with 2N HCl (50 mL)
  5. customforming a solid
  6. filtrationThe solid was collected by filtration
  7. washwashed with water

출처 및 근거

ORD 기록
ord-d9260cf37cde46febc80d0b25d151003
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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