Dimethylformamide → HCID 69222627, compound

HRID 32349Notes

Reaction equation

HRID 32349 reaction equation
N(C1N=[C:12]([C:14]2[N:18]([CH:19]([CH3:21])[CH3:20])[C:17](C=NOC)=[N:16][CH:15]=2)C=CN=1)C1C=CC=CC=1.[CH3:26][C:27]([N:29]([CH3:31])[CH3:30])=O.CN(C=[O:36])C>>[CH3:30][N:29]([CH3:31])[CH:27]=[CH:26][C:12]([C:14]1[N:18]([CH:19]([CH3:21])[CH3:20])[CH:17]=[N:16][CH:15]=1)=[O:36]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 31374DimethylacetamideHCID 867607262-Anilino-4-[1-isopropyl-2-(methoxyiminomethyl)imidazol-5-yl]pyrimidine

Product 1

HCID 69222627HCID 69222627, compoundYield 53%

Procedure

5-Acetyl-1-isopropylimidazole (Method 3; 15.3 g, 100 mmol) was dissolved in a mixture of DMF (90 ml) and DMF.DMA (150 ml) and the mixture was heated under reflux, under an atmosphere of nitrogen, for 18 hours. The reaction mixture was allowed to cool to ambient temperature and the product crystallised. The solid product was collected by filtration, washed with DMF.DMA and then ether and dried under vacuum at 40° C. to give the title compound (11 g, 53%) as a pale solid. NMR: 1.43 (d, 6H), 2.95 (m, 6H), 5.32 (m, 1H), 5.58 (d, 1H), 7.60 (m, 2H), 7.90 (s, 1H).

Workup

  1. temperatureunder reflux, under an atmosphere of nitrogen, for 18 hours
  2. customthe product crystallised
  3. filtrationThe solid product was collected by filtration
  4. washwashed with DMF
  5. dry with materialDMA and then ether and dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-fb1275bb44244879ac97398df8976de5
Source dataset
uspto-grants-2008_09
Patent number
US07427626B2

Reaction notes

Loading…