1-Propanol → 2-n-Propyloxy-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750854Notes

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:41])[CH2:39][CH3:40]>>[CH2:38]([O:41][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)[CH2:39][CH3:40]

Participants

Reactant 3

HCID 10311-Propanol

HCID 10255652HCID 10255652, compound

HCID 178418339Butyllithium

Product 1

HCID 597538952-n-Propyloxy-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 (50 mg, 0.1 mmol) was reacted with 2 equivalents each of n-butyl lithium and n-propanol by the procedure described in Reference Examples 6 and 7 to afford 2-(2-n-propyloxy-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. HPLC/MS: m/e=486 (M++1); Rt4.13 min. 1H-NMR 500 MHz (CDCl3): δ 0.96 (t, 3H), 1.73-1.79 (m, 2H), 4.13-4.18 (m, 2H), 7.18-7.30 (m, 7H), 7.40-7.43 (m, 1H), 7.60 (m, 1H), 8.55 (s, 2H).

Sources & evidence

ORD record: ord-082c0be6538743579ffa822e68a1403b
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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