HCID 21792675, compound → HCID 14035870, compound

HRID 2285569Notes

Reaction equation

HRID 2285569 reaction equation
C([O:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([S:24][CH3:25])=[N:18][C:19]=2[NH2:23])(=O)C1C=CC=CC=1>CN>[OH:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([S:24][CH3:25])=[N:18][C:19]=2[NH2:23]

Participants

3

Reactant 1

HCID 21792675HCID 21792675, compound

Product 1

HCID 14035870HCID 14035870, compound

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

A mixture of 2.20 g (6.12 mmol) of 9-(2-benzoyloxyethoxymethyl)-2-methylthioadenine and 100 ml of 40% aqueous methylamine was heated on a steam bath with occasional agitation for one hour. The solution was cooled and spin evaporated in vacuo. The resultant oil was leached with five 40 ml portions of hot ether to give a solid; yield, 1.31 g (84%), m.p. 174°-176°. Recrystallization from ethanol gave the analytical sample of 9-(2-hydroxyethoxymethyl)-2-methylthioadenine; λmax (ε×10-3) (10% EtOH in solvent) pH 1-270 (16.7),291 (sh) (11.9), H2O and pH 13-276 (15.2) nm; nmr (DMSO-d6), 2.49 (3H, S), 3.55 (4H, S), 4.65 (1H, br S), 5.55 (2H, S), 7.31 (2H, S), 8.15 (1H, S)ε.

Workup

  1. temperaturewas heated on a steam bath with occasional agitation for one hour
  2. temperatureThe solution was cooled
  3. customspin evaporated in vacuo
  4. customto give a solid
  5. customyield
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-4ceefeca985a47c49ec83a4134947144
Source dataset
uspto-grants-1982_04
Patent number
US04323573

Reaction notes

Loading…