Cyclopropanemethanol → HCID 59753923, compound

HRID 750863Notes

Reaction equation

HRID 750863 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.[CH:40]1([CH2:43][OH:44])[CH2:42][CH2:41]1>>[CH:40]1([CH2:43][O:44][C:5]2[N:10]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=3)[C:8]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:7]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[N:6]=2)[CH2:42][CH2:41]1

Participants

4

Reactant 3

HCID 75644CyclopropanemethanolHCID 10392549HCID 10392549, compoundHCID 178418339Butyllithium

Product 1

HCID 59753923HCID 59753923, 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 cyclopropylmethanol by the procedure described in Reference Example 6 and 7 to afford the title compound: HPLC/MS: m/e=533 (M++1); Rt=5.12 min. 1H-NMR 400 MHz (CDCl3): 0.56-0.61 (m, 2H), 1.23-1.30 (m, 2H), 1.57 (s, 1H), 4.01 (d, J=7 Hz, 2H), 6.90-6.94 (m, 1H), 7.04-7.10 (m, 1H), 7.12-7.28 (m, 7H), 7.35 (d, J=2 Hz, 1H).

Sources & evidence

ORD record
ord-7690513cbe0c4e958059b11cd7035ee5
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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