1-Butanol → 2-Amino-4-n-butoxy-6-chloromethylpyrmidine

HRID 3913Notes

Reaction equation

HRID 3913 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][Cl:10])[N:3]=1.CC(C)([O-])C.[K+].[CH2:17]([OH:21])[CH2:18][CH2:19][CH3:20]>>[NH2:1][C:2]1[N:7]=[C:6]([O:21][CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[C:4]([CH2:9][Cl:10])[N:3]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 201534884-Chloro-6-(chloromethyl)pyrimidin-2-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 545214932-Amino-4-n-butoxy-6-chloromethylpyrmidine

Conditions

Temperature
50 °C

Procedure

3,56 Parts of 2-amino-4-chloro-6-chloromethylpyrimidine and 2.24 parts of potassium t-butoxide were dissolved in 60 parts of n-butanol at room temperature then the solution was heated at 50° C. for 2 hours, with stirring. After this time, the solution was cooled and evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the organic phase was separated and washed three times with water then dried (MgSO4). Evaporation of the solvent gave the crude product which was purified by chromatography on silica (Merck Kieselgel 60) eluted with ether to give 2-amino-4-n-butoxy-6-chloromethylpyrmidine as an oil.

Workup

  1. temperatureAfter this time, the solution was cooled
  2. customevaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe organic phase was separated
  5. washwashed three times with water
  6. dry with materialthen dried (MgSO4)
  7. customEvaporation of the solvent
  8. customgave the crude product which
  9. customwas purified by chromatography on silica (Merck Kieselgel 60)
  10. washeluted with ether

Sources & evidence

ORD record
ord-c5c4f3d95a07449791cf3a5bbb4138ec
Source dataset
uspto-grants-1988_02
Patent number
US04723006

Reaction notes

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