Sodium Carbonate → 2-(4-Cyanophenyl)-5-bromopyrimidine

HRID 1954504Notes

Reaction equation

HRID 1954504 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)#[N:10].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>[C:9]([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)#[N:10]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 544971752-(4-Cyanophenyl)-5-bromopyrimidineYield 81.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (2.50 g, 8.77 mmol), 4-cyanophenylboronic acid 13 (1.42 g, 9.65 mmol), tetrakis(triphenylphosphine)palladium (304 mg, 0.26 mmol), DME (50 ml), aqueous 2M sodium carbonate (50 ml). The experimental procedure was as described for compound 4 to yield the cyanophenylpyrimidine 14 (1.85 g, 81%) (from MeOH), m.p. 222° C.; νmax /cm-1 (KBr) 2200 (CN), 1520, 1420s, 1120, 1015, 860 and 790; δ7.76 (2H, d, 3'- and 5'-H), 8.54 (2H, d, 2'- and 6'-H) and 8.83 (2H, s, 4- and 6-H); m/z 261 (M+), 259 (M+), 234 (M+ -HCN), 232 (M+ -HCN), 153 and 128.

Sources & evidence

ORD record
ord-5928f441578b499eb6e09b372aba43b2
Source dataset
uspto-grants-2000_09
Patent number
US06121448

Reaction notes

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