1-Butanol → HCID 59753932, compound

HRID 750855Notes

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:42])[CH2:39][CH2:40][CH3:41]>>[CH2:38]([O:42][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][CH2:40][CH3:41]

Participants

Reactant 3

HCID 2631-Butanol

HCID 10255652HCID 10255652, compound

HCID 178418339Butyllithium

Product 1

HCID 59753932HCID 59753932, compound

Procedure

2-Methylsulfonyl-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 86 (50 mg, 0.1 mmol) with 2 equivalents each of n-butyl lithium and n-butanol by the procedure described in Reference Examples 6 and 7 to afford 2-(2-n-butyloxy-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. HPLC/MS: m/e=500 (M++1); Rt=4.34 min. 1H-NMR 500 MHz (CDCl3): δ 0.93 (t, 3H), 1.40-1.46 (m, 2H), 1.70-1.75 (m, 2H), 4.22-4.26 (t, 2H), 7.18-7.30 (m, 7H), 7.40-7.42 (m, 1H), 7.57-7.60 (m, 1H), 8.54-8.55 (m, 2H).

Sources & evidence

ORD record: ord-8a72c5d69aff45b9a092e40a0d22c373
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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