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

HRID 1603295Notes

Reaction equation

HRID 1603295 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=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]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14]([C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 232970515-Bromo-2-(4-trifluoromethylphenyl)pyrimidineYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (2.64 g, 9.26 mmol), 4-(trifluoromethyl)phenylboronic acid 9 (2.29 g, 12.0 mmol), tetrakis(triphenylphosphine)palladium (53 mg, 0.046 mmol), DME (50 ml), 2M aqueous sodium carbonate (50 ml). The experimental procedure was as described for compound 4 to yield the trifluoromethylphenylpyrimidine 10 (1.58 g, 56%) (from MeOH), m.p. 167° C.; νmax /cm-1 (KBr) 1530, 1420, 1320s, 1165, 1120, 1070 and 1010; δ 7.74 (2H, d, J 8, 3'- and 5'-H), 8.52 (2H, d, J 8, 2'- and 6'-H) and 8.86 (2H, s, 4- and 6-H); m/z 304 (M+), 302 (M+),196 and 171.

Sources & evidence

ORD record
ord-b9db4ef2af154a9286e070f2bf2618eb
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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