Guanidine Hydrochloride → Methyl 2-aminopyrimidine-4-carboxylate

HRID 1890490Notes

Reaction equation

HRID 1890490 reaction equation
C(N(CC)CC)C.C(O[CH:13]=[CH:14][C:15](=O)[C:16]([O:18][CH3:19])=[O:17])CCC.Cl.[NH2:22][C:23]([NH2:25])=[NH:24]>C(#N)CC>[NH2:25][C:23]1[N:24]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:13][N:22]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 8471TriethylamineHCID 72805302HCID 72805302, compound

Product 1

HCID 57971148Methyl 2-aminopyrimidine-4-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (29 mL, 210 mmol) was added to a suspension of methyl 4-butoxy-2-oxo-3-butenate (37 g, 200 mmol, JP-A-2003-89690) and guanidine hydrochloride (23 g, 240 mmol) in propionitrile (50 mL), and the mixture was stirred for 4 hours at 100° C. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 18 g as the mixture of the title Reference Compound and the butyl ester form of the title Reference compound as a gray-white solid (Yield: 60%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. customto give 18 g
  4. additionas the mixture of the title Reference Compound

Sources & evidence

ORD record
ord-de4a33ba698a40799cab149d21a60538
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

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