HCID 178468507, compound → Ethyl 2-amino-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidine-5-carboxylate

HRID 2113180Notes

Reaction equation

HRID 2113180 reaction equation
[NH2:1][C:2]1[NH:3][CH:4]([CH:20]([CH3:22])[CH3:21])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([CH:20]([CH3:21])[CH3:22])[N:3]=1

Participants

4

Reactant 1

HCID 178468507HCID 178468507, compound

Product 1

HCID 24987285Ethyl 2-amino-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidine-5-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

Ethyl 2-amino-4-(4-fluorophenyl)-6-isopropyl-1,6-dihydropyrimidine-5-carboxylate (22.6 g) was dissolved in toluene (150 ml) and heated until a solution was obtained. Manganese dioxide (18.8 g) was added as a slurry in toluene (150 ml) and the mixture refluxed under azeotropic conditions for 6 hours until conversion was complete. A small amount of water was collected in the Dean and Stark trap. The slurry was filtered and the solvents removed by evaporation under reduced pressure to give ethyl 2-amino-4-(4-fluorophenyl)-6-isopropyl-pyrimidine-5-carboxylate as a crystalline solid in 96% yield.

Workup

  1. temperatureheated until a solution
  2. customwas obtained
  3. temperaturethe mixture refluxed under azeotropic conditions for 6 hours until conversion
  4. customA small amount of water was collected in the Dean and Stark trap
  5. filtrationThe slurry was filtered
  6. customthe solvents removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b7869e30088146a583523b46bfb3f278
Source dataset
uspto-grants-2009_04
Patent number
US07524955B2

Reaction notes

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