Potassium Carbonate → 2-Chloro-4-methylamino-5-methoxycarbonyl-pyrimidine

HRID 1374639Notes

Reaction equation

HRID 1374639 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][N:9]=1.Cl.[CH3:20][NH2:21]>O.CC(C)=O>[Cl:7][C:8]1[N:13]=[C:12]([NH:21][CH3:20])[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 23156323Methyl 2,4-dichloropyrimidine-5-carboxylate

Product 1

HCID 210775842-Chloro-4-methylamino-5-methoxycarbonyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

19.1 g of potassium carbonate in 50 ml water are added dropwise to 13 g of 2,4-dichloro-5-methoxycarbonyl-pyrimidine and 4.7 g of methylamine-hydrochloride in 500 ml acetone at 0 to 5° C. within one hour. Then the mixture is stirred for one hour in an ice bath. The acetone is largely removed in vacuo and the residue is distributed between water and ethyl acetate. Then the aqueous phase is extracted twice more with ethyl acetate. The combined organic phases are dried and evaporated down. The residue is separated by chromatography through a silica gel column with cyclohexane/ethyl acetate (2:1).

Workup

  1. customThe acetone is largely removed in vacuo
  2. extractionThen the aqueous phase is extracted twice more with ethyl acetate
  3. customThe combined organic phases are dried
  4. customevaporated down
  5. customThe residue is separated by chromatography through a silica gel column with cyclohexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0be8beac5a63477185418564f3320924
Source dataset
uspto-grants-2007_01
Patent number
US07166599B2

Reaction notes

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