Benzene → 1-[(Dimethylamino)carbonyl]-1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1722396Notes

Reaction equation

HRID 1722396 reaction equation
[CH3:1][O:2][C:3]1[NH:4][C:5]([CH3:24])=[C:6]([C:18]([O:20][CH:21]([CH3:23])[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.[CH2:25]([N:27]([CH2:30]C)[CH2:28]C)C.C(Cl)(Cl)=[O:33].C1C=CC=CC=1.CNC>ClCCl>[CH3:25][N:27]([CH3:30])[C:28]([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][CH:21]([CH3:22])[CH3:23])=[O:19])=[C:5]([CH3:24])[N:4]=[C:3]1[O:2][CH3:1])=[O:33]

Participants

7

Reactant 5

HCID 241BenzeneHCID 674DimethylamineHCID 6371PhosgeneHCID 8471TriethylamineHCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

Product 1

HCID 142570701-[(Dimethylamino)carbonyl]-1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (3.34 g, 10.0 mmol) and distilled triethylamine (6.3 ml, 45 mmol) in dichloromethane (10 ml) in an ice bath under argon was treated dropwise via syringe with 1.3M phosgene in benzene solution (9.2 ml, 12 mmol) over 3 to 5 minutes. After stirring at 0° C. for 1.5 hours, the reaction mixture was treated with 40% aqueous dimethylamine (3.3 ml, 15 mmol), capped with a septum, and stirred at room temperature for about 21/2 days. The reaction was then evaporated and partitioned between ethyl acetate and water. The organic phase was washed with saturated sodium chloride, dried (potassium carbonate), and evaporated to give the title compound (crude) as a brown oil (4.75 g).

Workup

  1. customcapped with a septum
  2. stirringstirred at room temperature for about 21/2 days
  3. customThe reaction was then evaporated
  4. custompartitioned between ethyl acetate and water
  5. washThe organic phase was washed with saturated sodium chloride
  6. dry with materialdried (potassium carbonate)
  7. customevaporated

Sources & evidence

ORD record
ord-52535b42b91e49148ca9b4cec8165271
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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