2-Aminopyrimidine → HCID 20544711, compound

HRID 2286971Notes

Reaction equation

HRID 2286971 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[C:19](Cl)=[O:20]>C(C(C)=O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[NH:1][C:19]([C:10]1[C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=[CH:18][C:9]=1[Cl:8])=[O:20]

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 20544693HCID 20544693, compound

Product 1

HCID 20544711HCID 20544711, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
10 °C

Procedure

280 ml of methyl ethyl ketone, 13 g of 2-amino-pyrimidine were put into a 500 ml balloon flask provided with a stirrer and a thermometer. The mixture was cooled to 10° C. and 28 g of ground 6-chloro-1,4-benzodioxane-5-carbonyl chloride was added and stirred for two hours, the temperature being allowed to rise to 20° C. The obtained solid was filtered off, washed with 30 ml of methyl ethyl ketone and then dissolved in 250 ml of boiling water. The solution was treated with 10 ml of 36° Bel caustic soda lye. After filtration 12 g of product were obtained and crystallized again from 150 ml of ethanol. 9.5 g of N-(2-pyrimidyl)-6-chloro-1,4-benzodioxane-5-carboxamide was obtained. (M.P.: 223° C. with decomposition). The structure was confirmed by nuclear magnetic resonance analysis.

Workup

  1. customprovided with a stirrer
  2. customto rise to 20° C
  3. filtrationThe obtained solid was filtered off
  4. washwashed with 30 ml of methyl ethyl ketone
  5. dissolutiondissolved in 250 ml of boiling water
  6. additionThe solution was treated with 10 ml of 36° Bel caustic soda lye
  7. filtrationAfter filtration 12 g of product
  8. customwere obtained
  9. customcrystallized again from 150 ml of ethanol

Sources & evidence

ORD record
ord-145fb86fa38f45999bac8e4519d1e503
Source dataset
uspto-grants-1981_05
Patent number
US04268512

Reaction notes

Loading…