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Acetic Acid → Acetic Acid 2-(4-bromomethyl-6-chloro-pyrimidin-5-yl)-ethyl ester

HRID 916657
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인쇄 미리보기

반응식

HRID 916657 반응식
[Br:1]Br.[CH2:3]([O:10][CH2:11][CH2:12][C:13]1[C:14]([Cl:20])=[N:15][CH:16]=[N:17][C:18]=1[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:21][C:22]([OH:24])=[O:23]>>[CH2:3]([O:10][CH2:11][CH2:12][C:13]1[C:18]([CH2:19][Br:1])=[N:17][CH:16]=[N:15][C:14]=1[Cl:20])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[Br:1][CH2:19][C:18]1[C:13]([CH2:12][CH2:11][O:23][C:22](=[O:24])[CH3:21])=[C:14]([Cl:20])[N:15]=[CH:16][N:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 24408BromineHCID 575033065-(2-Benzyloxy-ethyl)-4-chloro-6-methyl-pyrimidine

생성물 2

HCID 57503307Acetic Acid 2-(4-bromomethyl-6-chloro-pyrimidin-5-yl)-ethyl esterHCID 575033085-(2-Benzyloxy-ethyl)-4-bromomethyl-6-chloro-pyrimidine

반응 조건

온도
85 °C

실험 절차

Br2 (1.4 g, 8 mmol) is added drop wise to a stirred solution of 5-(2-benzyloxy-ethyl)-4-chloro-6-methyl-pyrimidine (2.1 g, 8 mmol) in HOAc (20 ml) at 85° C. After addition, the mixture is stirred at 85° C. for an additional 1 hour. The solvent is removed in vacuo and EtOAc (25 ml) and NaHCO3 (25 ml) are added to the residue. The layers are separated and the organic layer is washed with Na2S2O3 solution (sat. 15 ml) followed by brine (20 ml). The organic phase is dried (Na2SO4) and solvent evaporated. The resulting yellow oil is purified by flash column (EtOAc:hexane=6:1) to afford 5-(2-benzyloxy-ethyl)-4-bromomethyl-6-chloro-pyrimidine as a light yellow solid and acetic acid 2-(4-bromomethyl-6-chloro-pyrimidin-5-yl)-ethyl ester (162).

후처리

  1. additionAfter addition
  2. customThe solvent is removed in vacuo and EtOAc (25 ml) and NaHCO3 (25 ml)
  3. additionare added to the residue
  4. customThe layers are separated
  5. washthe organic layer is washed with Na2S2O3 solution (sat. 15 ml)
  6. dry with materialThe organic phase is dried (Na2SO4) and solvent
  7. customevaporated
  8. customThe resulting yellow oil is purified by flash column (EtOAc:hexane=6:1)

출처 및 근거

ORD 기록
ord-29969f96e3aa4ad7983d2005a9cfd829
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07271170B2

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