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Guanidine Hydrochloride → HCID 178459352, compound

HRID 2113178
Notes
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Reaction equation

HRID 2113178 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[CH3:15][CH:16]([CH3:26])[C:17](=O)[CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:4][C:3]1[NH:5][CH:17]([CH:16]([CH3:26])[CH3:15])[C:18]([C:19]([O:21][CH:22]([CH3:23])[CH3:24])=[O:20])=[C:11]([C:10]2[CH:13]=[CH:14][C:7]([F:6])=[CH:8][CH:9]=2)[N:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 57643949Propan-2-yl 4-methyl-3-oxopentanoate

Product 1

HCID 178459352HCID 178459352, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

Guanidine hydrochloride (12.1 g), 4-Fluorobenzaldehyde (7.0 g), isopropyl 4-methyl-3-oxo-pentanoate (8.9 g) and DMF (150 ml) were charged to a vessel equipped with a condenser and connected to a nitrogen line. The resultant mixture was stirred until a clear solution was obtained. Potassium carbonate (17.5 g) was charged and the mixture heated to 70° C. for 3 hours. The reaction mixture was cooled to ambient temperature, filtered, and the solvents removed by evaporation under reduced pressure. The resultant oil was triturated in water at 80° C. and cooled to give a slurry that was filtered and dried to give isopropyl 2-amino-4-(4-fluorophenyl)-6-isopropyl-1,6-dihydropyrimidine-5-carboxylate in 67% yield.

Workup

  1. customequipped with a condenser
  2. customwas obtained
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. customthe solvents removed by evaporation under reduced pressure
  6. customThe resultant oil was triturated in water at 80° C.
  7. temperaturecooled
  8. customto give a slurry that
  9. filtrationwas filtered
  10. customdried

Sources & evidence

ORD record
ord-2c90436d55d2455a934abbd4a3ca0673
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07524955B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes