Neopentyl alcohol → 2-(2,2-Dimethylpropyloxy)-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750852Notes

Reaction equation

HRID 750852 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:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>>[CH3:40][C:39]([CH3:42])([CH3:41])[CH2:38][O:43][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

Participants

4

Reactant 3

HCID 6404Neopentyl alcoholHCID 10255652HCID 10255652, compoundHCID 178418339Butyllithium

Product 1

HCID 104591522-(2,2-Dimethylpropyloxy)-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) was reacted with 2 equivalents each of n-butyl lithium and neopentyl alcohol by the procedure described in Reference Examples 6 and 7 to afford 2-(2,2-dimethylpropyloxy)-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine: HPLC/MS: m/e=514 (M++1); Rt4.48 min. 1H-NMR400 MHz (CDCl3): δ 1.20-1.30 (s, 9H), 3.88 (s, 2H), 7.15-7.28 (m, 7H), 7.40-7.43 (m, 1H), 7.58-7.61 (m, 1H), 8.52-8.56 (m, 2H).

Sources & evidence

ORD record
ord-c7236bb6bf2a4f6980597b2995a93aa8
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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