Hydrochloric Acid → HCID 20431326, compound

HRID 2412866Notes

Reaction equation

HRID 2412866 reaction equation
[Na].[Br-].[Li+].C([O:6][C:7](=O)[CH:8]([F:22])[CH2:9][CH2:10][N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][C:14]([NH2:21])=[N:15][C:16]=2[Cl:20])C.Cl.C(=O)([O-])O.[Na+]>>[NH2:21][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[CH2:10][CH2:9][CH:8]([F:22])[CH2:7][OH:6])=[C:16]([Cl:20])[N:15]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 54393076HCID 54393076, compound

Product 1

HCID 20431326HCID 20431326, compoundYield 60.4%

Conditions

Temperature
100 °C

Procedure

Sodium borohyride (15 mg) was dissolved in dry diethyleneglycoldiethylether (0.9 ml) and stirred. Finely powdered and dry lithiumbromide (34 mg) was added, followed after 1/2 hour by 4-(2-amino-6-chloropurin-9-yl)-2-fluorobutyric acid ethyl ester (100 mg). The reaction mixture was heated at 100° C. for 3 hours, then poured onto crushed ice (10 g) with added concentrated hydrochloric acid (0.5 ml) and stirred. The pH was adjusted to 6.5 by sodium hydrogen carbonate, the solution was evaporated in vacuo and the residue was redissolved in methanol-chloroform (40-60, 10 ml) and filtered. The solution was purified by chromatography on a silica gel column eluted with a methanol-chloroform gradient, to give the desired product (52 mg, 60%) TLC (silica gel, methanol-chloroform 40-60): Rf =0.66. UV (ethanol)λmax : 310 and 247 nm.

Workup

  1. additionpoured
  2. stirringstirred
  3. customthe solution was evaporated in vacuo
  4. dissolutionthe residue was redissolved in methanol-chloroform (40-60, 10 ml)
  5. filtrationfiltered
  6. customThe solution was purified by chromatography on a silica gel column
  7. washeluted with a methanol-chloroform gradient

Sources & evidence

ORD record
ord-9b26ab16dfa349c6955832983e4fc54d
Source dataset
uspto-grants-1985_01
Patent number
US04495190

Reaction notes

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