Hydrochloric Acid → HCID 13060223, compound

HRID 1982710Notes

Reaction equation

HRID 1982710 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([CH2:9][C:10]([O:12][CH2:13]C)=[O:11])[N:3]=1.[Na].Cl.[CH3:17][OH:18]>>[NH2:1][C:2]1[CH:7]=[C:6]([O:18][CH3:17])[N:5]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[N:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 5360545SodiumHCID 13060218HCID 13060218, compound

Product 1

HCID 13060223HCID 13060223, compound

Procedure

To a solution of ethyl 2-(4-amino-6-chloropyrimidin-2-yl)acetate (21.5 g) in methanol (200 ml) was added a solution of sodium metal (7.25 g) in methanol (130 ml) and the mixture was refluxed for 3.5 hours. The reaction mixture was cooled in an ice-salt bath and saturated with dry hydrogen chloride and then allowed to stand overnight at ambient temperature. The mixture was evaporated to dryness and the residue was dissolved in a mixture of ethyl acetate and a cold aqueous solution of sodium bicarbonate. The organic layer was separated out, washed with water, dried over anhydrous magnesium sulfate and and evaporated to give methyl 2-(4-amino-6-methoxypyrimidin-2-yl)acetate (14.2 g), mp 91°-94° C.

Workup

  1. temperaturethe mixture was refluxed for 3.5 hours
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate
  4. customThe organic layer was separated out
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d7284fc1e28847b1bb5f173f2298e449
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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