Potassium Carbonate → HCID 54393076, compound

HRID 2412865Notes

Reaction equation

HRID 2412865 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH:5]([F:9])[CH2:6][CH2:7]Br)[CH3:2].[NH2:11][C:12]1[N:20]=[C:19]2[C:15]([NH:16][CH:17]=[N:18]2)=[C:14]([Cl:21])[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([F:9])[CH2:6][CH2:7][N:18]1[CH:17]=[N:16][C:15]2[C:19]1=[N:20][C:12]([NH2:11])=[N:13][C:14]=2[Cl:21])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 54162042HCID 54162042, compound

Product 1

HCID 54393076HCID 54393076, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-fluorobutyric acid ethyl ester (0.23 g), 2-amino-6-chloropurine (0.19 g) and anhydrous potassium carbonate (0.15 g) were mixed and stirred in dimethylformamide (3.7 ml) at room temperature for two days. The solution was filtered and evaporated in vacuo. The residue was triturated with chloroform (4+2 ml) and the clear chloroform solution was evaporated to give the desired product (0.24 g, 72%). TLC (silica gel, i-propanol-water-conc. ammonia 8-1-1): Rf =0.76. NMR (CDCl3, Me4Si)δ: 1.26 (t, CH3); 2.4-2.5 (m, CH2); 4.2-4.3 (t and q, NCH2 and CO2CH2); 4.77 and 5.03 (CHF, J=51 Hz); 5.2 (NH2); 7.77 (8-CH).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated in vacuo
  3. customThe residue was triturated with chloroform (4+2 ml)
  4. customthe clear chloroform solution was evaporated

Sources & evidence

ORD record
ord-c20ee21ebe9f4495b0523fc60288cc36
Source dataset
uspto-grants-1985_01
Patent number
US04495190

Reaction notes

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