Isopropanol → HCID 59753938, compound

HRID 750858Notes

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.[CH:38]([OH:41])([CH3:40])[CH3:39]>>[CH: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)([CH3:40])[CH3:39]

Participants

Reactant 3

HCID 3776Isopropanol

HCID 10255652HCID 10255652, compound

HCID 178418339Butyllithium

Product 1

HCID 59753938HCID 59753938, compound

Procedure

2-Methylsulfonyl-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 86 (200 mg, 0.4 mmol) with 2 equivalents each of n-butyl lithium and isopropanol by the procedure described in Reference Examples 6 and 7 to afford the title compound: HPLC/MS: m/e=486 (M++1); Rt=4.11 min. 1H-NMR 400 MD (CDCl3): δ 1.32 (d, J=6 Hz, 6H), 5.01-5.06 (m, 1H), 7.17-7.30 (m, 6H), 7.36-7.37 (d, J=2 Hz, 1H), 7.36-7.41 (m, 1H), 7.56-7.59 (m, 1H), 8.53-8.55 (m, 2H).

Sources & evidence

ORD record: ord-1fb4604a5b174564a0326df138ee974b
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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