Neopentyl alcohol → HCID 178429022, compound

HRID 976111Notes

Reaction equation

HRID 976111 reaction equation
[Na].[NH2:2][C:3]1[N+:8]([O-:9])=[C:7]([CH3:10])[CH:6]=[C:5](Cl)[N:4]=1.[OH-].[Na+].[CH3:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17]>>[NH2:2][C:3]1[N+:8]([O-:9])=[C:7]([CH3:10])[CH:6]=[C:5]([O:17][CH2:16][C:15]([CH3:19])([CH3:18])[CH3:14])[N:4]=1

Participants

5

Reactant 4

HCID 6404Neopentyl alcoholHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 178426140HCID 178426140, compound

Product 1

HCID 178429022HCID 178429022, compound

Procedure

0.32 g of sodium is dissolved in 50 ml of 2,2-dimethyl-1-propanol in the heated state. 2 g (0.0125 mole) of 2-amino-4-methyl-6-chloropyrimidine 3-oxide are added and the reaction medium is brought to 105° C. for 22 hours. The mixture, still hot, is poured into 300 ml of 10% aqueous sodium hydroxide solution. The product is extracted with ethyl acetate and the organic phase is dried with sodium sulphate. It is concentrated and a brown oil is obtained. The latter is filtered on silica gel using an elution gradient with ethyl acetate and methanol. After evaporation, a solid crude product is obtained, which is recrystallized in an acetonitrile/water (98:2) mixture.

Workup

  1. extractionThe product is extracted with ethyl acetate
  2. dry with materialthe organic phase is dried with sodium sulphate
  3. concentrationIt is concentrated
  4. customa brown oil is obtained
  5. filtrationThe latter is filtered on silica gel using an elution gradient with ethyl acetate and methanol
  6. customAfter evaporation
  7. customa solid crude product is obtained
  8. customwhich is recrystallized in an acetonitrile/water (98:2) mixture

Sources & evidence

ORD record
ord-013c40b2838e4f67b2e5f20ac7dbc98b
Source dataset
uspto-grants-1997_03
Patent number
US05610302

Reaction notes

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