Methanol → HCID 10366150, compound

HRID 750872Notes

Reaction equation

HRID 750872 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1)(=[O:4])=[O:3].C([Li])CCC.[CH3:35][OH:36]>>[CH3:1][S:2]([C:5]1[N:10]=[C:9]([O:36][CH3:35])[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1)(=[O:4])=[O:3].[CH3:35][O:36][C:5]1[N:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 597538832,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine2×HCID 178418339Butyllithium

Product 2

HCID 10366150HCID 10366150, compoundHCID 10456101HCID 10456101, compound

Procedure

2,4-Bis(methylsulfonyl)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine from Reference Example 5 (2.0 g, 4.1 mmol) was reacted with 1.0 equivalent each of n-butyl lithium and methanol by the procedure described in Reference Example 6 and 7 to afford 2-(methylsulfonyl)-4-methoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine and 2-methoxy-4-(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)pyrimidine as a mixture: HPLC/MS: m/e=443 (M++1); Rt=3.57-3.89 min.

Sources & evidence

ORD record
ord-54511d816bf44074a4c7f88efbe410b8
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

Loading…