Hydrogen Peroxide → HCID 178444400, compound

HRID 1603309Notes

Reaction equation

HRID 1603309 reaction equation
[CH:1]1([CH2:7][CH2:8]C2C=CN=C(C3C=CC=CC=3)N=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.B(OC)(OC)OC.OO.[F:35][C:36]1[C:41]([F:42])=[C:40]([CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:39]=[CH:38][C:37]=1[C:48]1[N:53]=[CH:52][C:51]([OH:54])=[CH:50][N:49]=1>C1COCC1>[F:35][C:36]1[C:41]([F:42])=[C:40]([CH2:43][CH2:44][C@H:45]2[CH2:8][CH2:7][C@H:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:47][CH2:46]2)[CH:39]=[CH:38][C:37]=1[C:48]1[N:49]=[CH:50][C:51]([OH:54])=[CH:52][N:53]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 196090982-(2,3-Difluoro-4-pentylphenyl)-5-pyrimidinolHCID 70099580HCID 70099580, compoundHCID 178418339Butyllithium

Product 1

HCID 178444400HCID 178444400, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

--Quantities bromopyrimidine 16 (3.72 g, 8.25 mmol), 1.6M butyllithium (5.7 ml, 9.1 mmol), trimethyl borate (1.9 ml, 16.5 mmol), THF (80 ml), 30% hydrogen peroxide (3.7 ml, 33 mmol). 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 hydroxypyrimidine 48 (1.82 g, 57%) (from MeOH), m.p. 157.3° C.; νmax /cm-1 (KBr) 2920, 2720, 2580, 1505, 1430, 1280, 1240 and 1180 δ 0.85 (7H, m), 1.05-1.38 (10H, m), 1.50 (2H, m), 1.73 (4H, t), 2.68 (2 H, t, ArCH2), 7.01 (1H, ddd, 5'-H), 7.55 (1H, ddd, 6'-H), 8.37 (2H, s, 4- and 6-H) and 9.7 (1H, br s); m/z 388 (M+), 317 (M+ -C5H11), 235, 222 and 204.

Workup

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

Sources & evidence

ORD record
ord-89f64e2c6702466cb390b46dd5faa33f
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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