Sodium Carbonate → 2-(2'-Fluoro-4'-octyloxyphenyl)-5-bromopyrimidine

HRID 1603293Notes

Reaction equation

HRID 1603293 reaction equation
BrC1C=NC(I)=NC=1.FC1C=C(OCCCCCCCC)C=CC=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[F:34][C:35]1[C:40](F)=[C:39]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:38]=[CH:37][C:36]=1[C:51]1[N:56]=[CH:55][C:54]([Br:57])=[CH:53][N:52]=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:34][C:35]1[CH:40]=[C:39]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:38]=[CH:37][C:36]=1[C:51]1[N:52]=[CH:53][C:54]([Br:57])=[CH:55][N:56]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 70066515-Bromo-2-iodopyrimidineHCID 105160192-Fluoro-4-octyloxyphenylboronic acidHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 536614472-(2'-Fluoro-4'-octyloxyphenyl)-5-bromopyrimidineYield 69%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (4.05 g, 14.2 mmol), 2-fluoro-4-octyloxyphenylboronic acid 5 (4.57 g, 17.0 mmol), tetrakis(triphenylphosphine)palladium (328 mg, 0.28 mmol), 2M sodium carbonate (50 ml), DME (50 ml). The experimental procedure was as described for compound 4 to yield the monofluorophenylpyrimidine 6 (3.68 g, 69%) (from MeOH), m.p. 71.6° C.; νmax /cm-1 (KBr) 2920, 2850, 1610, 1410, 1270, 1125 and 830; δ 0.90 (3H, t, Me), 1.20-1.55 (10H, m), 1.82 (2H, quint, OCH2CH2), 4.00 (2H, t, OCH2), 6.75 (2H, m, 3'- and 4'-H), 8.06 (1H, t, 6'-H) and 8.85 (2H, s, 4- and 6-H); m/z 382 (M+), 380 (M+), 270 (M+ -C8H16), 268 (M+ -C8H16) and 137.

Sources & evidence

ORD record
ord-e9fff20ce0ca4e3fb410eabe718f9a80
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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