3,5-Dimethyl-4-hydroxybenzonitrile → 4-(2-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

HRID 1516854노트

반응식

HRID 1516854 반응식
[H-].[Na+].[OH:3][C:4]1[C:11]([CH3:12])=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[CH3:13].[Cl:14][C:15]1[N:16]=[C:17](Cl)[C:18]2[N:23]([CH3:24])[CH:22]=[CH:21][C:19]=2[N:20]=1>CN1C(=O)CCC1.O>[Cl:14][C:15]1[N:16]=[C:17]([O:3][C:4]2[C:5]([CH3:13])=[CH:6][C:7]([C:8]#[N:9])=[CH:10][C:11]=2[CH3:12])[C:18]2[N:23]([CH3:24])[CH:22]=[CH:21][C:19]=2[N:20]=1

참가 물질

6

반응물 3

HCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 24758Sodium hydrideHCID 147277632,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidine

생성물 1

HCID 576936264-(2-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile수율 89.5%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

To a stirred solution of NaH (42.1 mg, 1.05 mmol) in dry NMP (2.5 mL) was added 4-hydroxy-3,5-dimethylbenzonitrile (154.7 mg, 1.05 mmol) and stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 2,4-dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (211.3 mg, 1.05 mmol) in dry NMP (2.7 mL) and heated at 160° 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 (3:1-1:1), to give the product as a light yellow solid (294 mg, 85%).

후처리

  1. temperatureheated at 160° 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 (3:1-1:1)

출처 및 근거

ORD 기록
ord-30f5e7d58d4c46f7b4f7e4c5fab32e66
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227601B2

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