Sodium Carbonate → 5-Bromo-2-(4-fluorophenyl)pyrimidine

HRID 1603298Notes

Reaction equation

HRID 1603298 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].FC1C(F)=C(OCCCCCCCC)C=CC=1C1N=CC(Br)=CN=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 232970645-Bromo-2-(4-fluorophenyl)pyrimidineYield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (4.00 g, 14.0 mmol), 4-fluorophenylboronic acid 19 (2.44 g, 17.4 mmol), tetrakis(triphenylphosphine)palladium (324 mg, 0.28 mmol), DME (50 ml), aqueous 2M sodium carbonate (50 ml). The experimental procedure was as described for compound 4. The crude product was purified by flash chromatography (5% ethyl acetate-light petroleum) to give the fluorophenylpyrimidine 20 (3.3 g, 94%) (from MeOH), m.p. 155.5° C.; νmax /cm-1 (KBr) 1595, 1525, 1505, 1400s, 1220, 1150 and 785; δ 7.15 (2H, dd, J9, 3'- and 5'-H), 8.41 (2H, dd, J9 and 4, 2'- and 6'-H) and 8.80 (2H, s, 4- and 6-H); m/z 254 (M+), 252 (M+), 227 (M+ -HCN), 225 (M+ -HCN), 146 and 121.

Workup

  1. customThe crude product was purified by flash chromatography (5% ethyl acetate-light petroleum)

Sources & evidence

ORD record
ord-88b02c397a7545b1a819206de29d25f8
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

Loading…