Dimethylformamide → HCID 10137846, compound

HRID 1393971Notes

Reaction equation

HRID 1393971 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2N)[C:5](=[O:15])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:32]([O:34][C:35](=[O:39])[CH:36](Br)[CH3:37])[CH3:33].C[N:41](C=O)C>>[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([NH:41][CH:36]([CH3:37])[C:35]([O:34][CH2:32][CH3:33])=[O:39])=[CH:21][CH:20]=2)[C:5](=[O:15])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 69220149HCID 69220149, compound

Product 1

HCID 10137846HCID 10137846, compound

Procedure

To a solution of 1-[2-ethyl-6-oxo-4-phenyl-1,6-dihydro-1-pyrimidinyl]-2-(aminophenoxy)ethane (1.9 g, 5.67 mmol) (Ref. U.S. Pat. No. 6,310,069) in dry DMF (20 mL) was added K2CO3 and stirred at RT for 30 min. To this ethyl-2-bromopropanoate (1.54 g, 8.51 mmol), was added and the mixture was stirred at 50° C. for 14 h. The reaction mixture was filtered, washed with EtOAc and the combined filtrates were washed with water and extracted with EtOAc. The organic layer was dried over Na2SO4, evaporated the solvent and the crude compound was purified by column chromatography by eluting with 25% EtOAc:pet. ether to give the title compound as a brownish low melting solid (mp: 40° C., 1.867 g, 76%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 14 h
  2. filtrationThe reaction mixture was filtered
  3. washwashed with EtOAc
  4. washthe combined filtrates were washed with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated the solvent
  8. customthe crude compound was purified by column chromatography
  9. washby eluting with 25% EtOAc

Sources & evidence

ORD record
ord-178b0da571844cc7810e258137ab6fd2
Source dataset
uspto-grants-2008_03
Patent number
US07348334B2

Reaction notes

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