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

HRID 1603300Notes

Reaction equation

HRID 1603300 reaction equation
BrC1C=NC(I)=NC=1.FC1C=C(OCC2C=CC=CC=2)C=CC=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[F:33][C:34]1[C:39](F)=[C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]C)[CH:37]=[CH:36][C:35]=1[C:50]1[N:55]=[CH:54][C:53]([Br:56])=[CH:52][N:51]=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:33][C:34]1[CH:39]=[C:38]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:37]=[CH:36][C:35]=1[C:50]1[N:51]=[CH:52][C:53]([Br:56])=[CH:54][N:55]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27377864-Benzyloxy-2-fluorophenylboronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 540225402-(2'-Fluoro-4'-benzyloxyphenyl)-5-bromopyrimidineYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (5.05 g, 17.7 mmol), 2-fluoro-4-benzyloxyphenylboronic acid 27 (4.84 g, 19.7 mmol), tetrakis(triphenylphosphine)palladium (680 mg, 0.59 mmol), 2M sodium carbonate (50 ml), DME (50 ml). The experimental procedure was as described for compound 4 to yield the benzyloxyfluorophenylpyrimidine 28 (3.34 g, 53%) (from MeOH), m.p. 124.2° C.; νmax /cm-1 (KBr) 3030, 2860, 1615s, 1430, 1420, 1320, 1215, 1020 and 830, δ 5.22 (2H, s, CH2), 6.75-6.89 (2H, m, 3'- and 5'-H), 7.32-7.48 (5H, m, Ph), 8.06 (1H, t, 6'-H) and 8.85 (2H, s, 4-and 6-H); m/z 360 (M+), 358 (M+), 269 (M+ -PhCH2), 267 (M+ -PhCH2), 247, 221 and 91.

Sources & evidence

ORD record
ord-0c5c90137cc74f7d8fec43641ed1e557
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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