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

HRID 376762Notes

Reaction equation

HRID 376762 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]CCCCCC)=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[C:37]([F:44])[C:36]=1[F:45])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[CH:7]=[N:6][C:5]([C:8]3[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=3)=[N:4][CH:3]=2)=[C:37]([F:44])[C:36]=1[F:45])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 152187534-Benzyloxy-2,3-difluorobenzeneboronic acidHCID 178694045-Bromo2-(6-dodecyloxypyridin-3-yl)pyrimidine

Product 1

HCID 178693985-(4-Benzyloxy-2,3-difluorophenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidineYield 49.1%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The reaction of 6 mmol of 5-bromo-2-(6-dodecyloxypyridin-3-yl)pyrimidine, 6 mmol of 4-benzyloxy-2,3-difluorophenylboronic acid, 12 mmol of sodium carbonate 0.06 mmol of bis(dibenzylideneacetone)palladium(0) and 0.12 mmol of triphenylphosphine in 50 ml of toluene, 25 ml of ethanol and 25 ml of water is carried out analogously to the procedure indicated for Example 1a). Corresponding chromatographic purification gives 1.4 g (42%) of a colorless solid, m.p. 115° C., cl.p. 172° C.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-2cf8b4c3f53b479bb896742e282250cc
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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