Dimethylformamide → HCID 13338435, compound

HRID 2417688Notes

Reaction equation

HRID 2417688 reaction equation
Cl[C:2]1[C:3]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[NH2:14][CH:15]([CH3:19])[C:16](=[O:18])[CH3:17].C(N([CH2:25][CH3:26])CC)C.CN(C)C=[O:30]>>[CH3:12][N:11]1[C:3]2[C:2]([NH:14][CH:15]([C:16]3([CH3:17])[O:30][CH2:25][CH2:26][O:18]3)[CH3:19])=[N:7][C:6]([CH3:8])=[N:5][C:4]=2[C:9]([CH3:13])=[N:10]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 44721173-aminobutan-2-oneHCID 133384077-Chloro-1,3,5-trimethyl-1H-pyrazolo[4,3-d]pyrimidine

Product 1

HCID 13338435HCID 13338435, compoundYield 87%

Procedure

A mixture of 9.5 g (0.05 mol) of 7-chloro-1,3,5-trimethyl-1H-pyrazolo[4,3-d]pyrimidine (Example 3), 10 g (0.075 mol) of 3-amino-2-butanone, ethylene ketal, and 14 ml of triethylamine in 30 ml of dimethylformamide is stirred at 50°-55° C. for 24 hours. The mixture is evaporated in vacuo, the residue is dissolved in methylene dichloride and washed with ammonium hydroxide solution. The organic layer is dried over MgSO4 and evaporated in vacuo. The residue is crystallized from pet ether to give 12.6 g (87%) of 1,3,5-trimethyl-N-[1-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-pyrazol[4,3-d]pyrimidin-7-amine, mp 101°-103° C.

Workup

  1. customThe mixture is evaporated in vacuo
  2. dissolutionthe residue is dissolved in methylene dichloride
  3. washwashed with ammonium hydroxide solution
  4. dry with materialThe organic layer is dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue is crystallized from pet ether

Sources & evidence

ORD record
ord-9fa8df680800474a888a1a2228cdd425
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

Loading…