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

HRID 1722401
Notes
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Reaction equation

HRID 1722401 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.C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33].C1C=CC=CC=1.[CH2:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[Cl-].[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[N:8]([C:32]([NH:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:33])[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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 241BenzeneHCID 5234Sodium ChlorideHCID 6371PhosgeneHCID 7504BenzylamineHCID 8471TriethylamineHCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

Product 1

HCID 14855106
1,6-Dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 (5.00 g, 15.0 mmol; see Example 2A) and dry triethylamine (6.27 ml, 45 mmol) in dichloromethane (45 ml) in an ice bath under argon was treated with a 1.2M solution of phosgene in benzene (15.0 ml, 18.0 mmol) via syringe. After stirring 4.0 hours at 0° C., the reaction was treated with benzyl amine (2.46 ml, 22.5 mmol) and stirred at ambient temperature overnight. The reaction was treated with water and saturated sodium chloride. The organic phase was evaporated and flash chromatographed (3% ethyl acetate in dichloromethane) to give the title compound as a yellow foam (6.20 g) TLC (5% ethyl acetate/dichlorolmethane) major spot, Rf =0.70.

Workup

  1. stirringstirred at ambient temperature overnight
  2. customThe organic phase was evaporated
  3. customflash chromatographed (3% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-9ff8d6bdff9f46049dac2c5f377ec371
Source dataset
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04855301

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes