Potassium Carbonate → HCID 54133619, compound

HRID 2412861Notes

Reaction equation

HRID 2412861 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[CH2:12]([O:14][C:15](=[O:21])[CH:16]([OH:20])[CH2:17][CH2:18]Br)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([O:14][C:15](=[O:21])[CH:16]([OH:20])[CH2:17][CH2:18][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[Cl:11])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 19019164HCID 19019164, compound

Product 1

HCID 54133619HCID 54133619, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-6-chloropurine (0.509 g, 3.00 mmole), 4-bromo-2-hydroxybutyric acid ethyl ester (0.633 g, 3.00 mmole; prepared according to Example 1) and anhydrous potassium carbonate (0.415 g, 3.00 mmole) were mixed with 10 g of dimethyl formamide and the mixture stirred at room temperature during 65 hours. The mixture was then filtered and the filtrate evaporated at a pressure of 0.1 mm Hg. The crystalline residue was triturated with 8 ml of chloroform and the undissolved material filtered off and washed with 2 ml of chloroform. The material obtained was then triturated with 5 ml of water and the undissolved material filtered off and washed with 2 ml of water. Recrystallization from 11 ml of ethanol gave 0.360 g product. M.P. 163°-4° C. (uncorr.) UV spectra(ethanol): λmax (nm) 311, 248. Analyses--Found: C 43.90; H 4.78; Cl 11.72; N 23.52; O 15.90%. Calculated for C11H14ClN5O3 : C 44.08; H 4.71; Cl 11.83; N 23.37; O 16.01%.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated at a pressure of 0.1 mm Hg
  3. customThe crystalline residue was triturated with 8 ml of chloroform
  4. filtrationthe undissolved material filtered off
  5. washwashed with 2 ml of chloroform
  6. customThe material obtained
  7. customwas then triturated with 5 ml of water
  8. filtrationthe undissolved material filtered off
  9. washwashed with 2 ml of water
  10. customRecrystallization from 11 ml of ethanol

Sources & evidence

ORD record
ord-63ccf260a8174e18b70ac5e319ec3111
Source dataset
uspto-grants-1985_01
Patent number
US04495190

Reaction notes

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