3,5-Dichlorobenzylic alcohol → 2-(3,5-Dichlorobenzyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

HRID 750838Notes

Reaction equation

HRID 750838 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:5][N:4]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH2:28][OH:29]>>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH2:28][O:29][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 432363,5-Dichlorobenzylic alcoholHCID 597539142-Methylthio-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

Product 1

HCID 597539452-(3,5-Dichlorobenzyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

Procedure

2-Methylthio-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)pyrimidine from Reference Example 3 was reacted with 3,5-dichlorobenzyl alcohol according to the procedure described in Example 59 to afford 2-(3,5-dichlorobenzyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (HRf): HPLC/MS: m/e=510 (M++1); Rt=5.12 min; 1H-NMR 400 MHz (CDCl3): δ 5.45 (s, 2H), 7.03 (d, J=9 Hz, 2H), 7.21-7.40 (m, 6H), 7.42 (d, J=2 Hz, 2H), 8.60 (s, 1H).

Sources & evidence

ORD record
ord-af8a417d4fcc461dacf6291228c5cb43
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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