HCID 21792675, compound → HCID 14035870, compound

HRID 614948Notes

Reaction equation

HRID 614948 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) δ.

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-6a79be73441e4a7eba9971d599c818af
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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