Isobutanol → 2-(iso-Butyloxy)-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750857Notes

Reaction equation

HRID 750857 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.[CH2:38]([OH:42])[CH:39]([CH3:41])[CH3:40]>>[CH2:38]([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)[CH:39]([CH3:41])[CH3:40]

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 10255652HCID 10255652, compoundHCID 178418339Butyllithium

Product 1

HCID 597538782-(iso-Butyloxy)-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Procedure

2-Methylsulfonyl-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 86 (100 mg, 0.2 mmol) with 2 equivalents each of n-butyl lithium and iso-butyl alcohol by the procedure described in Reference Examples 6 and 7 to afford the title compound: HPLC/MS: m/e=500 (M++1); Rt=4.31 min. 1H-NMR 500 MHz (CDCl3): δ 0.96 (d, J=6 Hz, 6H), 2.02-2.10 (m, 1H), 4.01 (d, J=7 Hz, 2H), 7.18-7.30 (m, 6H), 7.39 (s, 1H), 7.40-7.43 (m, 1H), 7.58-7.60 (m, 1H), 8.55 (s, 2H).

Sources & evidence

ORD record
ord-a9ce4a2c89064a808c1815dfdc825e13
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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