4-Nitrophenyl chloroformate → 5-Methyl 1-(4-nitrophenyl) 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,5(6H)-pyrimidinedicarboxylate

HRID 1452655Notes

Reaction equation

HRID 1452655 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:13][C:12]([O:14][CH3:15])=[N:11][C:10]([CH3:16])=[C:9]2[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:13]([C:22]([O:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:23])[C:12]([O:14][CH3:15])=[N:11][C:10]([CH3:16])=[C:9]2[C:17]([O:19][CH3:20])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 178498443HCID 178498443, compound

Product 1

HCID 105272225-Methyl 1-(4-nitrophenyl) 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,5(6H)-pyrimidinedicarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of methyl 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-5-pyrimidinecarboxylate (1.76 g, 6.34 mmol) and 4-dimethylaminopyridine (12.7 mmol, 1.55 g) in anhydrous CH2Cl2 (20.0 mL) was added solution of 4-nitrophenyl chloroformate (4.47 g, 22.2 mmol) in CH2Cl2 (20.0 mL) at 23° C. The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (hexanesiethyl acetate 4:1). The product was obtained as yellow syrup, which upon trituration with hexanes became a white powder (2.40 g, 84.3%). The crude product was used in next step without further purification.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (hexanesiethyl acetate 4:1)
  5. customThe product was obtained as yellow syrup, which upon trituration with hexanes
  6. customThe crude product was used in next step without further purification

Sources & evidence

ORD record
ord-e0322ba4644b49aa83d7f4108e774005
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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