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Water → Tert-butyl (4-{4-[(3S)-3-methylmorpholin-4-yl]-6-[(phenylsulfonyl)methyl]pyrimidin-2-yl}phenyl)carbamate

HRID 2353658
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HRID 2353658 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=1.O.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:36][CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(COC)OC.C(O)C>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[CH:5]=[C:4]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=[C:2]([C:34]2[CH:35]=[CH:36][C:37]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[CH:38][CH:39]=2)[N:7]=1
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참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734617tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamateHCID 593800404-(benzenesulfonylmethyl)-2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine

생성물 1

HCID 59379956Tert-butyl (4-{4-[(3S)-3-methylmorpholin-4-yl]-6-[(phenylsulfonyl)methyl]pyrimidin-2-yl}phenyl)carbamate
수율 67.9%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 6228Dimethylformamide용매HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

(3S)-4-{2-Chloro-6-[(phenylsulfonyl)methyl]pyrimidin-4-yl}-3-methylmorpholine (3.2 g, 8.70 mmol) was dissolved in a solution of 18% DMF in a mixture of 7:3:2 dimethoxyethane:water:ethanol (36 mL). Tert-butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (4.16 g, 13.05 mmol), 2M sodium carbonate solution (8 mL) and dichlorobis(triphenylphosphine) palladium catalyst (306 mg, 0.43 mmol) were then added and the reaction refluxed at 90° C. for 2 hours under a nitrogen atmosphere. The reaction was allowed to cool to room temp then partitioned between ethyl acetate (20 mL) and water (20 mL). The organics were dried over magnesium sulphate, filtered and concentrated in vacuo. The crude solid was chromatographed on silica, eluting with 0-30% ethyl acetate in DCM to give the desired material as a beige solid (3.1 g).

후처리

  1. temperatureto cool to room temp
  2. customthen partitioned between ethyl acetate (20 mL) and water (20 mL)
  3. dry with materialThe organics were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude solid was chromatographed on silica
  7. washeluting with 0-30% ethyl acetate in DCM

출처 및 근거

ORD 기록
ord-63201f23f7734ddeab8b64a73db931d8
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07750003B2

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