Toluene → (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol

HRID 79137

반응식

HRID 79137 반응식
[Cl:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(OCC)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 59419388(4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol수율 59%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (20.0 g, 86 mmol) in dichloromethane (400 mL) at −78° C. was added diisobutylaluminum hydride, 1.0 M in toluene (172 mL, 172 mmol). The reaction was allowed to warm to 0° C. over 2 h. To the reaction was added a 20% Rochelle's (1600 mL) and diethyl ether (750 mL). The emulsion was stirred for 30 min. The organics were sequestered and the aqueous was extracted further with diethyl ether (2×500 mL). The combined organics were washed with water (500 mL), brine (500 mL), dried over MgSO4, and concentrated in vacuo and filtered through a plug of silica eluting with 1:1; ethyl acetate:CH2Cl2 to obtain compound 223 (9.6 g, 59% yield). 1H NMR (500 MHz, CDCl3) δ 8.55 (s, 1 H) 4.75 (d, J=5.87 Hz, 2 H) 2.58 (s, 3 H) 2.06-2.25 (m, J=5.14 Hz, 1H) ppm.

후처리

  1. extractionthe aqueous was extracted further with diethyl ether (2×500 mL)
  2. washThe combined organics were washed with water (500 mL), brine (500 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered through a plug of silica eluting with 1:1

출처 및 근거

ORD 기록
ord-e664bf7ae4104507b016d46c466eb36a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841312B2

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