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(Diethylamino)sulfur trifluoride → 5-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine

HRID 925176
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HRID 925176 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:16]([OH:18])[CH3:17])[CH:15]=2)=[CH:4][N:3]=1.[CH3:24]CN(S(F)(F)F)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([CH:16]=[CH2:17])=[CH:15][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22].[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([CH:16]([O:18][CH3:24])[CH3:17])=[CH:15][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 573291161-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanol

생성물 2

HCID 573289585-(2-Isopropyl-4-methoxy-5-vinyl-phenoxy)-pyrimidine-2,4-diamine수율 3%HCID 595986985-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine
수율 4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanol (1.613 g, 5.3 mmol) in 30 ml CH2Cl2 at −78° C. was added DAST (0.935 g, 5.8 mmol). After stirring 1.5 h, saturated NaHCO3 was added and the mixture was extracted by CH2Cl2. The combined organics were washed with brine and dried with Na2SO4, filtered and concentrated in vacuo. Purification via silica gel chromatography (95:5 CH2Cl2/MeOH) gave 5-(2-Isopropyl-4-methoxy-5-vinyl-phenoxy)-pyrimidine-2,4-diamine (0.044 g, 3%) as a foam ([MH]+=301) and 5-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine (0.075 g, 4%) as foam. [MH]+=303.

후처리

  1. extractionthe mixture was extracted by CH2Cl2
  2. washThe combined organics were washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (95:5 CH2Cl2/MeOH)

출처 및 근거

ORD 기록
ord-ad522038365c430e9e58da774bea8aa1
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284279B2

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