Pyridine → HCID 22725143, compound

HRID 2085417Notes

Reaction equation

HRID 2085417 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][C:13]([O:15][CH3:16])=[N:12][C:11]([CH2:17][CH3:18])=[C:10]2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:37]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:14]([C:36]([O:38][C:39]3[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=3)=[O:37])[C:13]([O:15][CH3:16])=[N:12][C:11]([CH2:17][CH3:18])=[C:10]2[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 178436962HCID 178436962, compound

Product 1

HCID 22725143HCID 22725143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a well-stirred solution of benzyl 6-(3,4-difluorophenyl)-4-ethyl-2-methoxy-1,6-dihydro-5-pyrimidinecarboxylate (27.5 g, 68.75 mmol) and pyridine (9.2 mL) in CH2Cl2 (300 mL) was added 4-nitrophenyl chloroformate (14.49 g, 82.5 mmol) at room temperature. The reaction mixture was stirred for 4 h and then washed with 10% aqueous KOH solution (2×150 mL). The organic layer was separated and dried over Na2SO4. The solvent was removed in vacuo and the residue was used in the next step without further purification: 1H NMR (CDCl3) δ 1.24 (t, J=7.2 Hz, 3H), 2.81-2.98 (m, 3H), 3.97 (s, 3H), 5.14 (ABq, 2H), 6.28 (s, 3H), 7.03-7.29 (m, 8H), 7.35 (d, J=9.2 Hz, 2H), 8.26 (d, J=9.2 Hz, 2H).

Workup

  1. washwashed with 10% aqueous KOH solution (2×150 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-9c4830cd22f54b4fa7b5e6985aba9724
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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