Potassium Carbonate → Tert-butyl 5-(2,4-dichlorophenyl)-7-methyl-2-(oxazol-5-yl)imidazo[1,2-a]pyrimidine-6-carboxylate

HRID 1868473Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([CH:18]=[O:19])[N:17]=[C:13]2[N:12]=[C:11]([CH3:20])[C:10]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].S([CH2:38][N+:39]#[C-:40])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([C:18]3[O:19][CH:40]=[N:39][CH:38]=3)[N:17]=[C:13]2[N:12]=[C:11]([CH3:20])[C:10]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of tert-butyl 5-(2,4-dichlorophenyl)-2-formyl-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (90 mg, 0.22 mmol) in MeOH (4 mL) was added tosyl methyl isocyanide (52 mg, 0.27 mmol) and K2CO3 (61 mg, 0.44 mmol). After heating to 60° C. for 30 min, the reaction was concentrated under reduced pressure and purified by silica gel chromatography to provide tert-butyl 5-(2,4-dichlorophenyl)-7-methyl-2-(oxazol-5-yl)imidazo[1,2-a]pyrimidine-6-carboxylate (65 mg, 66%) as a light yellow solid.

Workup

concentrationthe reaction was concentrated under reduced pressure
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-8b1d3b35899742a999db2e423e3e861d
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635699B2

Reaction notes

Loading…