Cyclohexanemethanol → 2-(Cyclohexylmethoxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

HRID 750837Notes

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

Participants

Reactant 2

HCID 7507Cyclohexanemethanol

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

Product 1

HCID 597539132-(Cyclohexylmethoxy)-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 cyclohexylmethanol according to the procedure described in Example 59 to afford 2-(cyclohexylmethoxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (HRf): HPLC/MS: m/e=447 (M++1); Rt=5.17 min; 1H-NMR 400 MHz (CDCl3): δ 1.02-1.20 (m, 2H), 1.20-1.40 (m, 4H), 1.64-1.80 (m, 3H), 1.81-1.98 (m, 2H), 4.23 (d, J=9 Hz, 2H), 7.01 (d, J=9 Hz, 2H), 7.22-7.30 (m, 4H), 7.38 (d, J=2 Hz,1H), 8.58 (s, 1H).

Sources & evidence

ORD record: ord-c55e36db9318404192215bc47b0fdf8c
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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