3,4-Difluorobenzyl alcohol → 2-(3,4-Difluorobenzyloxy)-4-(amino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750809Notes

Reaction equation

HRID 750809 reaction equation
CS([C:5]1[N:10]=[C:9]([NH2:11])[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:6]=1)(=O)=O.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:31][OH:32]>>[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:31][O:32][C:5]1[N:10]=[C:9]([NH2:11])[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:6]=1

Participants

3

Reactant 2

HCID 5228333,4-Difluorobenzyl alcoholHCID 691989512-(Methylsulfonyl)-4-(amino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Product 1

HCID 102551082-(3,4-Difluorobenzyloxy)-4-(amino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Procedure

The title compound obtained by treating 2-(methylsulfonyl)-4-(amino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Example 32, Step A,) with 3,4-difluorobenzyl alcohol by the same general procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 80/20 hexanes/ethyl acetate) afforded 2-(3,4-difluorobenzyloxy)-4-(amino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. HPLC/MS: m/e=494 (M++1); Rt=3.91 min. 1H-NMR 500 MHz (CDCl3): δ 5.10 (bs, 2H), 5.38 (s, 2H), 7.0-7.10 (m, 2H), 7.11-7.23 (m, 6H), 7.15-7.19 (m, 2H).

Sources & evidence

ORD record
ord-5b4bae449eaf4839a3703b1f29d322f8
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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