(+-)-2-Butanol → 2-(Sec-butyloxy)-4-(3-pyridyloxy)-5-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750856Notes

Reaction equation

HRID 750856 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:6]=1)(=O)=O.C([Li])CCC.[CH:38]([OH:42])([CH2:40][CH3:41])[CH3:39]>>[CH:38]([O:42][C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:6]=1)([CH2:40][CH3:41])[CH3:39]

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 10255652HCID 10255652, compoundHCID 178418339Butyllithium

Product 1

HCID 597539372-(Sec-butyloxy)-4-(3-pyridyloxy)-5-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)pyrimidine

Procedure

2-Methylsulfonyl-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 86 (50 mg, 0.1 mmol) was reacted with 2 equivalents each of n-butyl lithium and sec-butanol by the procedure described in Reference Examples 6 and 7 to afford 2-(sec-butyloxy)-4-(3-pyridyloxy)-5-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)pyrimidine: HPLC/MS: m/e=500 (M++1); Rt=4.26 min. 1H-NMR 500 MHz (CDCl3): δ 0.91 (t, 3H), 1.29 (d, J=6 Hz, 3H), 1.56-1.64 (m, 1H), 1.71-1.80(m, 1H), 4.81-4.88 (m, 1H), 7.18-7.30 (m, 6H), 7.36-7.38 (t, 1H), 7.40-7.43 (m, 1H), 7.60 (m, 1H), 8.52-8.56 (m, 2H).

Sources & evidence

ORD record
ord-34ceabd3afc24e60b7047086a2f5889a
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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