1,1-Dimethoxyethyl(dimethyl)amine → HCID 131724959, compound
Reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([NH2:12])=[O:11])=[N:6][C:5]=12.CO[C:15](OC)([N:17]([CH3:19])[CH3:18])[CH3:16]>>[CH3:18][N:17]([C:15](=[N:12][C:10]([C:7]1[CH:8]=[CH:9][N:4]2[CH:3]=[CH:2][N:1]=[C:5]2[N:6]=1)=[O:11])[CH3:16])[CH3:19]Participants
Procedure
A mixture of imidazo[1,2-α]pyrimidine-7-carboxylic acid amide (310 mg) and N,N-dimethylacetamide dimethylacetal (270 mg) was heated at reflux for 16 h then cooled to ambient temperature. The reaction was then partitioned between dichloromethane and water. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to give imidazo[1,2-α]pyrimidine-7-carboxylic acid [1-(N,N-dimethylamino)ethylidene]amide as a brown oil. This oil was dissolved in 70% aqueous acetic acid (120 ml) and 1,4-dioxane (60 ml). A solution of hydroxylamine in water (40 wt. %, 0.15 ml) was then added and the mixture heated at 100° C. for 2 h then cooled to ambient temperature. This reaction mixture was dissolved in 50% methanol in dichloromethane and pre-adsorbed onto silica. Purification on silica gel eluting with dichloromethane (+1% conc. ammonia) on a gradient of methanol (2-5%) gave 7-(3-methyl-[1,2,4]oxadiazol-5-yl)imidazo[1,2-α]pyrimidine as a yellow solid (110 mg, 29% over 2 steps): δH (360 MHz, DMSO) 2.43 (3H, s), 7.76 (1H, d, J 7), 8.02 (1H, d, J 1), 8.19 (1H, d, J 1), 9.22 (1H, d, J 7).
Workup
- temperaturewas heated
- temperatureat reflux for 16 h
- customThe reaction was then partitioned between dichloromethane and water
- dry with materialThe organic phase was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-bbfbe813866045439207b1aa6e238732
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900215B2
Reaction notes
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