Sodium Carbonate → HCID 57965012、化合物

HRID 1931596ノート

反応式

HRID 1931596 の反応式
[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][CH:12]([NH:15][NH2:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[Cl:17][C:18]1[C:23]([CH:24]=O)=[C:22](Cl)[N:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:17][C:18]1[N:19]=[CH:20][N:21]=[C:22]2[N:15]([CH:12]3[CH2:13][CH2:14][CH:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:10][CH2:11]3)[N:16]=[CH:24][C:23]=12

参加物

5

反応物 3

HCID 10340Sodium Carbonate2 回HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde2 回HCID 57964979HCID 57964979、化合物2 回

生成物 1

HCID 57965012HCID 57965012、化合物収率 36%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
140 °C

実験手順

A mixture of [4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-hydrazine (Intermediate 12; 230 mg, 1.0 mmol), 4,6-dichloro-pyrimidine-5-carbaldehyde (Intermediate 16; 182 mg, 1.0 mmol) and sodium carbonate (218 mg, 2.1 mmol) in acetonitrile was heated in the microwave at 140° C. for 10 min. Saturated aqueous sodium carbonate was added and the reaction mixture was filtered. The filtrate was extracted with ethyl acetate, and the combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 10% ethyl acetate/hexanes to give 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (125 mg, 35%) as a white solid. Mass spectrum M+=346.

後処理

  1. filtrationthe reaction mixture was filtered
  2. extractionThe filtrate was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography
  7. washeluting with 10% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-0fdd78d6ab674a2dbd81a5c03cbed1c8
出典データセット
uspto-grants-2012_05
特許番号
US08188098B2

反応ノート

読み込み中…