Triethylamine → 3-(2,2-Dimethyl-1-oxopropyl)-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, ethyl ester

HRID 1590298Notes

Reaction equation

HRID 1590298 reaction equation
C[O:2][C:3]1[NH:4][C:5]([CH3:23])=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:40](Cl)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]>ClCCl>[CH3:42][C:41]([CH3:44])([CH3:43])[C:40]([N:8]1[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([CH3:23])[NH:4][C:3]1=[O:2])=[O:45]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 62493Pivaloyl chlorideHCID 139125831,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester

Product 1

HCID 867467173-(2,2-Dimethyl-1-oxopropyl)-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.96 g., 3.0 mmole), dry triethylamine (1.25 ml., 9.0 mmole), and dimethylaminopyridine (36 mg., 0.3 mmole) in dichloromethane (12 ml.) under argon is treated with pivaloyl chloride (0.44 ml., 3.6 mmole). After stirring for 45 minutes at room temperature, the reaction mixture is evaporated. The residue is taken up in tetrahydrofuran/methanol (10 ml. each) and treated with 2N hydrochloric acid (6.0 ml., pH 1). After stirring at room temperature for 3.0 hours, the reaction is quenched with saturated sodium bicarbonate, partially evaporated and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride and evaporated. Flash chromatography and crystallization from dichloromethane/isopropyl ether gives the title compound as white crystals (420 mg. , m. p. 155°-156°. TLC(silica gel; ethyl acetate:hexane, 1:1)Rf =0.67.

Workup

  1. customthe reaction mixture is evaporated
  2. additioneach) and treated with 2N hydrochloric acid (6.0 ml., pH 1)
  3. stirringAfter stirring at room temperature for 3.0 hours
  4. customthe reaction is quenched with saturated sodium bicarbonate
  5. custompartially evaporated
  6. extractionextracted with ethyl acetate
  7. washThe organic phase is washed with saturated sodium chloride
  8. customevaporated
  9. customFlash chromatography and crystallization from dichloromethane/isopropyl ether

Sources & evidence

ORD record
ord-98b2611ecfbf4c4795d62d4917581552
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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