4-Chlorobenzylamine → HCID 54431387, compound

HRID 476840Notes

Reaction equation

HRID 476840 reaction equation
C1(C)C=CC(S(O[CH2:11][C@H:12]2[O:16][C@@H:15]([N:17]3[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]3=[O:19])[CH2:14][C@@H:13]2[OH:26])(=O)=O)=CC=1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>CN(C=O)C>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:34][CH2:11][C@H:12]2[O:16][C@@H:15]([N:17]3[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]3=[O:19])[CH2:14][C@@H:13]2[OH:26])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 7302460((2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 54431387HCID 54431387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 396 mg of 5'-O-(p-toluenesulphonyl)thymidine and 1.5 ml of 4-chlorobenzylamine in 2 ml of DMF was stirred at 80° C. for 2 hours. The solvent was removed by evaporation and the residue was triturated with diethyl ether. The resulting solid was recrystallized from ethanol to yield 56 mg of 5'-(4-chlorobenzylamino)-5'-deoxythymidine, mp 179°-180° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with diethyl ether
  3. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-c252c35b259f408e90dc775dd2fe6136
Source dataset
uspto-grants-1989_12
Patent number
US04886785

Reaction notes

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