Isobutanol → HCID 59753953, compound

HRID 750862Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:7]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[N:6]=1)(=O)=O.C([Li])CCC.[CH2:40]([OH:44])[CH:41]([CH3:43])[CH3:42]>>[CH2:40]([O:44][C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:7]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[N:6]=1)[CH:41]([CH3:43])[CH3:42]

Participants

Reactant 3

HCID 6560Isobutanol

HCID 10392549HCID 10392549, compound

HCID 178418339Butyllithium

Product 1

HCID 59753953HCID 59753953, compound

Procedure

2-Methylsulfonyl-4-(3,4-difluorophenoxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 20 (65 mg, 0.12 mmol) was reacted with 2 equivalents each of n-butyl lithium and isobutyl alcohol by the procedure described in Reference Example 6 and 7 to yield the title compound: HPLC/MS: m/e=535 (M++1); Rt=5.28 min. 1H-NMR 400 MHz (CDCl3): 0.97 (d, J=7 Hz, 6H), 2.07 (m, 1H), 4.01 (d, J=7 Hz, 2H), 6.90-6.94 (m, 1H), 7.05-7.10 (m, 1H), 7.12-7.28 (m, 7H), 7.34 (d, J=2 Hz, 1H).

Sources & evidence

ORD record: ord-094a674c0d7d4594a22d0ffcdc0b99a6
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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