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

HRID 222154노트

반응식

HRID 222154 반응식
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

참가 물질

6

반응물 4

HCID 7509Benzyl mercaptanHCID 8028TetrahydrofuranHCID 178418725HCID 178418725, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-66ba66f2e393456ca40a45eedadbc85a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207177B2

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