m-Chloroperbenzoic acid → 3-[(Dimethylamino)carbonyl]-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1722409Notes

Reaction equation

HRID 1722409 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][N:13]([CH3:48])[C:14]([N:16]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:20]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[C:19]([CH3:37])[N:18]=[C:17]1SCC1C=CC(OC)=CC=1)=[O:15]>ClCCl.C(OCC)(=O)C>[CH3:48][N:13]([CH3:12])[C:14]([N:16]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:20]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[C:19]([CH3:37])[NH:18][C:17]1=[O:6])=[O:15]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57133964(+)-3,4-Dihydro-3-[(dimethylamino)carbonyl]-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Product 1

HCID 148017303-[(Dimethylamino)carbonyl]-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Chloroperoxybenzoic acid (3 eq, 2.0 mmol, 349 mg) was added to a solution of (-)-3,4-dihydro-3-[(dimethylamino)carbonyl]-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester in dry dichloromethane (6.7 ml) at 0° C. under a nitrogen atmosphere. The reaction was stirred overnight at room temperature, and a precipitate formed. The mixture was diluted with ethyl acetate (15 ml) and washed with 1N hydrochloric acid (twice), 1N sodium hydroxide (twice) and water. The combined organic layers were dried over magnesium sulfate, filtered, and reduced in vacuo to afford an oil, 390 mg. Flash chromatography on 39 g silica gel (2:1:ethyl acetate:hexanes) afforded the product as an oil. The oil was allowed to stand under ether for a 48 hour period, and was then triturated to produce a white crystalline solid, 144 mg (55%), melting point 152°-153° C. [α]D =-128.6° (c=1.2, chloroform).

Workup

  1. customa precipitate formed
  2. washwashed with 1N hydrochloric acid (twice), 1N sodium hydroxide (twice) and water
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customto afford an oil, 390 mg

Sources & evidence

ORD record
ord-6663fbb117ad4de19134ac3d9c12cf5c
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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