Sodium Carbonate → 2-(4-Benzyloxy-2,3-difluorophenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

HRID 376763Notes

Reaction equation

HRID 376763 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18](Br)=[CH:17][N:16]=2)=[C:11]([F:22])[C:10]=1[F:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][N:34]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:36]3[CH:35]=[N:34][C:33]([O:32][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:38][CH:37]=3)=[CH:17][N:16]=2)=[C:11]([F:22])[C:10]=1[F:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 178694022-[4-(Benzyloxy)-2,3-difluorophenyl]-5-bromopyrimidineHCID 224127982-Octyloxy-5-pyridineboronic acid

Product 1

HCID 178694012-(4-Benzyloxy-2,3-difluorophenyl)-5-(6-octyloxypyridin-3-yl)pyrimidineYield 61%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The reaction of 35 mmol of 2-(4-benzyloxy-2,3-difluorophenyl)-5-bromopyrimidine, 44 mmol of 2-octyloxypyridine-5-boronic acid, 70 mmol of sodium carbonate and 0.4 mmol of tetakis(triphenylphosphine)palladium(0) in 120 ml of toluene, 60 ml of ethanol and 60 ml of water is carried out analogously to the procedure indicated for Example 1a). Corresponding chromatographic purification and recrystallization from ethyl acetate gives 10.7 g (61%) of colorless crystals, m.p. 120° C., cl.p. 182-183° C.

Workup

  1. custompurification and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-bd44ee1f85224c19aec19a07c2b9daf4
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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