Hydrogen Peroxide → 2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-hydroxypyrimidine

HRID 1603302Notes

Reaction equation

HRID 1603302 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:18]1[N:23]=[CH:22][C:21](Br)=[CH:20][N:19]=1.C([Li])CCC.B(OC)(OC)[O:31]C.OO.FC1C(F)=C(CCCCC)C=CC=1C1N=CC(O)=CN=1>CCCCCC.C1COCC1>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:18]1[N:23]=[CH:22][C:21]([OH:31])=[CH:20][N:19]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 196090982-(2,3-Difluoro-4-pentylphenyl)-5-pyrimidinolHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidineHCID 178418339Butyllithium

Product 1

HCID 218324672-(2',3'-Difluoro-4'-octyloxyphenyl)-5-hydroxypyrimidineYield 56.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

--Quantities: difluorophenylbromo-pyrimidine 4 (4.30 g, 10.8 mmol), 2.5M butyllithium (4.5 ml, 11.3 mmol), trimethyl borate (2.6 ml, 22.6 mmol), THF (100 ml), hexane (30 ml), 30% hydrogen peroxide (5.4 ml, 44 mmol) ether (200 ml). The experimental procedure was as described for compound 33. The crude product was purified by flash chromatography (10 to 30% ethyl acetate-light petroleum) to give the difluorophenyl-5-hydroxypyrimidine 35 (2.04 g, 56%) [from light petroleum (b.p. 60-80° C.)], m.p. 84-85° C.; νmax /cm-1 (KBr) 3 100br, 2920, 2850, 1620, 1560, 1510, 1475, 1430, 1300, 1285, 1200 and 1085; δ 0.91 (3H, t, Me), 1.19-1.52 (10H, m), 1.32 (2H, quint, OCH2CH2), 4.05(2H, t, OCH2), 6.79 (1H, ddd, J8, 7 and 2, 5'-H), 7.59 (1H, ddd, J8.5, 7 and 2, 6'-H) and 8.38 (2 H, s, 4- and 6-H); m/z 336 (M+), 335, 237, 223, 208, 195 and 155.

Workup

  1. customThe crude product was purified by flash chromatography (10 to 30% ethyl acetate-light petroleum)

Sources & evidence

ORD record
ord-57ddbe99ff1648fda4c59a6fb5da776c
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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