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

HRID 916657
ノート
印刷プレビュー

反応式

HRID 916657 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 2

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

反応条件

温度
85 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-29969f96e3aa4ad7983d2005a9cfd829
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07271170B2

反応ノート

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