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

HRID 916657
Notes
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Reaction equation

HRID 916657 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 2

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

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-29969f96e3aa4ad7983d2005a9cfd829
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07271170B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes