Cyclobutanol → 2-Cyclobutyloxy-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750853Notes

Reaction equation

HRID 750853 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]1([OH:42])[CH2:41][CH2:40][CH2:39]1>>[CH:38]1([O:42][C:5]2[N:10]=[C:9]([O:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:8]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:7]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])[N:6]=2)[CH2:41][CH2:40][CH2:39]1

Participants

4

Reactant 3

HCID 76218CyclobutanolHCID 10255652HCID 10255652, compoundHCID 178418339Butyllithium

Product 1

HCID 597539012-Cyclobutyloxy-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 (30 mg, 0.06 mmol) with 2 equivalents each of n-butyl lithium and cyclobutyl alcohol by the procedure described in Reference Examples 6 and 7 to afford 2-(2-cyclobutyloxy-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine: HPLC/MS: m/e=498 (M++1); Rt4.16 min. 1H-NMR 400 MHz (CDCl3): δ 1.70-1.85 (m, 2H), 2.16-2.28 (m, 4H), 4.93 (m, 1H), 7.14-7.38 (m, 7H), 7.40-7.42 (m, 1H), 7.55-7.58 (m, 1H), 8.52-8.54 (m, 2H).

Sources & evidence

ORD record
ord-8a14b0d6920b493ea30769ef2ea89031
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

Loading…