Water → HCID 22725170, compound

HRID 1976580Notes

Reaction equation

HRID 1976580 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[NH:15][C:14]([O:25][CH3:26])=[N:13][C:12]=1[CH2:27][CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31].O.[OH-].[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[N:15]([C:30]([O:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:31])[C:14]([O:25][CH3:26])=[N:13][C:12]=1[CH2:27][CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 178436961HCID 178436961, compound

Product 1

HCID 22725170HCID 22725170, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of 5-(benzyloxycarbonyl)-1,6-dihydro-2-methoxy-4-ethyl-6-(2,4-difluorophenyl)pyrimidine (22.5 g, 59.3 mmol) and 4-(N,N-dimethylamino)pyridine (9.3 g, 75.8 mmol) in CH2Cl2 (200 mL) was added powdered 4-nitrophenyl chloroformate (15.3 g, 75.8 mmol) at 0° C. The reaction mixture was stirred for 12 h at room temperature and then water (50 mL) was added. The pH of the aqueous layer was adjusted to 10-11 by the addition of 6 N sodium hydroxide. The dichloromethane layer was separated and dried (Na2SO4). Solvent was evaporated in vacuo and the residue was purified by column chromatography (SiO2, dichloromethane/hexane, 20%-50%) to yield the product as a viscous oil (32.0 g, 98%).

Workup

  1. customThe dichloromethane layer was separated
  2. dry with materialdried (Na2SO4)
  3. customSolvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography (SiO2, dichloromethane/hexane, 20%-50%)

Sources & evidence

ORD record
ord-a09d431be0814c348aaaa7a13a9eb0df
Source dataset
uspto-grants-2001_05
Patent number
US06228861B1

Reaction notes

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