Sodium hydride → 2-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidine

HRID 1516850ノート

反応式

HRID 1516850 の反応式
[H-].[Na+].[CH:3]1([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[C:8]([CH3:14])[CH:7]=2)[CH2:5][CH2:4]1.[Cl:15][C:16]1[N:17]=[C:18](Cl)[C:19]2[NH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CN1C(=O)CCC1.O>[Cl:15][C:16]1[N:17]=[C:18]([O:13][C:9]2[C:8]([CH3:14])=[CH:7][C:6]([CH:3]3[CH2:5][CH2:4]3)=[CH:11][C:10]=2[CH3:12])[C:19]2[NH:24][CH:23]=[CH:22][C:20]=2[N:21]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 53750532,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidineHCID 576935554-Cyclopropyl-2,6-dimethylphenol

生成物 1

HCID 576936052-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidine収率 10.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

To a stirred suspension of NaH (25 mg, 0.64 mmol) in dry NMP (1.5 mL) was added 4-cyclopropyl-2,6-dimethylphenol (103 mg, 0.64 mmol) and the resolution mixture was stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (120 mg, 0.64 mmol) in dry NMP (1.7 mL) and heated at 90° C. for 16 h. After completion of the reaction, the resulting mixture was diluted with water and washed with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (4:1-2:1), to give the product as a light yellow solid (20.2 mg, 8%).

後処理

  1. temperatureheated at 90° C. for 16 h
  2. customAfter completion of the reaction
  3. washwashed with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with hexanes/ethyl acetate (4:1-2:1)

出典と根拠

ORDレコード
ord-ccb2945576734e0688a96ea7a69e4997
出典データセット
uspto-grants-2012_07
特許番号
US08227601B2

反応ノート

読み込み中…