Sodium hydride → HCID 59753946, compound

HRID 750874Notes

Reaction equation

HRID 750874 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:6]=1)(=O)=O.[H-].[Na+].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:35][OH:36]>>[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:35][O:36][C:5]1[N:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:6]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 5228333,4-Difluorobenzyl alcoholHCID 59753898HCID 59753898, compound

Product 1

HCID 59753946HCID 59753946, compound

Procedure

2-(Methylsulfonyl)-4-ethoxy-5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)pyrimidine (LRf from Example 123) was reacted with 2 equivalents each of sodium hydride and 3,4-difluorobenzyl alcohol by the procedure described in Example 16 to afford the title compound: HPLC/MS: m/e=521 (M++1); Rt=4.90 min. 1H-NMR 400 MHz (CDCl3): δ 1.35 (t, 3H), 4.45-4.55 (dd, J=9 Hz, J=7 Hz, 2H), 5.20 (s, 2H), 7.02-7.21 (m, 9H), 7.35 (d, J=2 Hz, 1H).

Sources & evidence

ORD record
ord-611b17b436904b17ab4cd89da550d8fc
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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