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Bromine → 7-Bromomethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 898707
Notes
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Reaction equation

HRID 898707 reaction equation
[Br:1]Br.[CH3:3][C:4]1[N:9]=[CH:8][N:7]2[N:10]=[CH:11][N:12]=[C:6]2[C:5]=1[CH2:13][CH2:14][CH3:15]>CC(O)=O>[Br:1][CH2:3][C:4]1[N:9]=[CH:8][N:7]2[N:10]=[CH:11][N:12]=[C:6]2[C:5]=1[CH2:13][CH2:14][CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24408BromineHCID 534715537-Methyl-8-propyl-[1,2,4]triazolo[1,5-C]pyrimidine

Product 1

HCID 575033117-Bromomethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Br2 (0.153 ml, 3 mmol) is added dropwise to a solution of 7-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine (3 mmol) heated at 100° C. in HOAc (10 ml). After the addition, the mixture is stirred at 100° C. overnight. The solvent is removed in vacuo and the residue dissolved in EtOAc (15 ml), washed with Na2S2O3 solution (sat. 5 ml), followed by NaHCO3 (10 ml), and brine (10 ml). The organic phase is dried (Na2SO4) and evaporated. The resulting yellow oil is purified by PTLC, which provides the title compound.

Workup

  1. additionAfter the addition
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc (15 ml)
  4. washwashed with Na2S2O3 solution (sat. 5 ml)
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customevaporated
  7. customThe resulting yellow oil is purified by PTLC, which

Sources & evidence

ORD record
ord-17eaa9ceafd441438d1045638ffd60ea
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07351826B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes