Acetic Anhydride → 2-(3,4-Difluorobenzyloxy)-4-(acetylamino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-pyrimidine

HRID 750811Notes

Reaction equation

HRID 750811 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][O:6][C:7]1[N:12]=[C:11]([NH2:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:8]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][O:6][C:7]1[N:12]=[C:11]([NH:13][C:33](=[O:35])[CH3:34])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 102551082-(3,4-Difluorobenzyloxy)-4-(amino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Product 1

HCID 103470652-(3,4-Difluorobenzyloxy)-4-(acetylamino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title compound was obtained by treating 2-(3,4-difluorobenzyloxy)-4-amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Example 33) with acetic anhydride and catalytic DMAP by the same general procedure described in Example 34. Workup and flash column chromatography on silica gel (eluted with 80/20 hexanes/ethyl acetate) afforded the desired product. HPLC/MS: m/e=536 (M++1); Rt=4.5 min. 1H-NMR 500 MHz (CDCl3): δ 2.56 (s, 3H), 5.45 (s, 2H), 7.03-7.27 (m, 9H), 7.38 (d, J=2 Hz, 1H), 8.05 (bs, 1H).

Sources & evidence

ORD record
ord-b8a1db15ca8b4eff8ae5f43ee9b62c06
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

Loading…