1-Butanol → 2-(n-Butyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

HRID 750835Notes

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.[CH2:24]([OH:28])[CH2:25][CH2:26][CH3:27]>>[CH2:24]([O:28][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)[CH2:25][CH2:26][CH3:27]

Participants

Reactant 2

HCID 2631-Butanol

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

Product 1

HCID 100470022-(n-Butyloxy)-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 n-butanol according to the procedure described in Example 59 to afford 2-(n-butyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (HRf): HPLC/MS: m/e=407 (M++1); Rt=4.80 min; 1H-NMR 400 MHz (CDCl3): δ 1.00 (t, 3H), 1.50-1.6 (m,2H), 1.80-1.85 (m, 2H), 4.41-4.44 (t, 2H), 7.01 (d, J=9 Hz, 2H), 7.21-7.25 (m, 5H), 8.58 (s, 1H).

Sources & evidence

ORD record: ord-4f2141b71a8145ceb01324b3b8b9f5e2
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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