tert-Butyl methyl ether → 4-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidine

HRID 575638노트

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HRID 575638 반응식
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][N:5]=[C:4](SC)[N:3]=1.[CH:15]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:26][S:27]([O-:29])=O.[Na+].[Na+].CC(OC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)=[CH:6][N:5]=[C:4]([S:27]([CH3:15])(=[O:29])=[O:26])[N:3]=1

참가 물질

6

반응물 4

HCID 15413tert-Butyl methyl etherHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 1180241114-Chloro-5-(cyclopropylmethoxy)-2-methylsulfanylpyrimidine

생성물 1

HCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidine수율 78.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To the title compound of step 3 (19.0 g, 82.60 mmol) in dry CH2Cl2 (200 mL) at 0° C., m-CPBA (42.62 g, 247.80 mmol) was added over 15 min. The mixture was stirred at 0° C. for 30 min and at r.t. overnight. Sat.aq. Na2SO3 (100 mL) was added and CH2Cl2 extractive work up was carried out. Trituration with MTBE (300 mL) gave the title compound (17 g, 78.3% yield) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.37 (s, 1H), 4.13 (d, J=6.8 Hz, 2H), 3.33 (s, 3H), 1.39-1.35 (m, 1H), 0.79-0.74 (m, 2H), 0.49-0.45 (m, 2H). LCMS: 263.0 (M+1)+

출처 및 근거

ORD 기록
ord-f73e5778be1944469d0a00d81ba25250
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034900B2

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