Benzyl mercaptan → 4-(Benzylsulfanyl)-7h-pyrrolo[2,3-d]pyrimidine

HRID 222154ノート

反応式

HRID 222154 の反応式
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.O(C(C)(C)C)[K].C1COCC1.[C:22]1([CH2:28][SH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[CH2:28]([S:29][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 7509Benzyl mercaptanHCID 8028TetrahydrofuranHCID 178418725HCID 178418725、化合物HCID 178418922HCID 178418922、化合物

生成物 1

HCID 2658264-(Benzylsulfanyl)-7h-pyrrolo[2,3-d]pyrimidine収率 79%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
85 °C

実験手順

To a round bottomed flask with a stir bar was added 4-chloro-1H-pyrrolo-[2,3-d]pyrimidine (5.07 g, 33.0 mmol), 1.00 M of KO-t-Bu in THF (49.5 mL, 49.5 mmol), and benzenemethanethiol (5.81 mL, 49.5 mmol) in isopropyl alcohol (350 mL). The reaction mixture was heated to reflux at 85° C. under an atmosphere of nitrogen. After 48 h, the reaction mixture was cooled and solvent was removed in vacuo. To the residue was added water (300 mL) and the solution was filtered to collect the resulting white solid. The solid was washed with diethyl ether and MeOH and dried under vacuum to afford the product as a white solid (6.29 g, 79% yield). LC/MS: Rt=1.68 min, ES+ 242 (FA standard). Reference: Pathak, A. K., Pathak, V., Seitz, L. E., Suling, W. J., Reynolds, R. C. J. Med. Chem., 2004, 47, 273-276.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperaturethe reaction mixture was cooled
  3. customsolvent was removed in vacuo
  4. additionTo the residue was added water (300 mL)
  5. filtrationthe solution was filtered
  6. customto collect the resulting white solid
  7. washThe solid was washed with diethyl ether and MeOH
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-66ba66f2e393456ca40a45eedadbc85a
出典データセット
uspto-grants-2012_06
特許番号
US08207177B2

反応ノート

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