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

HRID 1508910ノート

反応式

HRID 1508910 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].[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d9260cf37cde46febc80d0b25d151003
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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