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Guanidine Hydrochloride → 4-Pyrimidinecarboxylic acid, 2-amino-, methyl ester

HRID 602297
Notes
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Reaction equation

HRID 602297 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 8471TriethylamineHCID 72805302HCID 72805302, compound

Product 1

HCID 579711484-Pyrimidinecarboxylic acid, 2-amino-, methyl esterYield 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-75d1a1db9a334ec6b2d8775becfed182
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906511B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes