3,4-Difluorobenzyl alcohol → HCID 59753928, compound

HRID 750825Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]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.[F:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[F:47])[CH2:42][OH:43]>>[F:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[F:47])[CH2:42][O:43][C:5]1[N:10]=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]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

Participants

Reactant 3

HCID 5228333,4-Difluorobenzyl alcohol

HCID 69197999HCID 69197999, compound

HCID 178418339Butyllithium

Product 1

HCID 59753928HCID 59753928, compound

Procedure

2-(Methylsulfonyl)-4-(cyclohexyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (LRf product) (Example 52, Step A), (24 mg, 0.045 mmol) was reacted with 1 equivalent each of n-butyl lithium and 3,4-difluorobenzyl alcohol by the procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 93/7 hexanes/ethyl acetate) afforded the title compound. HPLC/MS: m/e=577 (M++1); Rt=5.34 min; 1H-NMR 500 MHz (CDCl3): 1.28-1.40 (m, 3H), 1.40-1.55 (m, 2M), 1.50-1.60 (m, 2H), 1.60-1.70 (m, 2H), 1.8-1.90 (m, 2H), 5.26 (m, J=4 Hz, 1H), 5.40 (s, 2H), 7.03 (d, J=8 Hz, 2H), 7.05 (d, J=1 Hz), 7.15-7.27 (m, 5H), 7.34 (d over multiplet, J=2 Hz, 2H).

Sources & evidence

ORD record: ord-8b551f2a3085463aa440b7708c6221ad
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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