Ammonia → HCID 20156937, compound

HRID 986629Notes

Reaction equation

HRID 986629 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7](Br)[N:8]2[CH2:11][O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[C:4]([NH2:19])[N:3]=1.[NH3:20]>CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([NH2:20])[N:8]2[CH2:11][O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[C:4]([NH2:19])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20156938HCID 20156938, compound

Product 1

HCID 20156937HCID 20156937, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1.153 g (3.46 mM) of 2-[(2,6-diamino-8-bromo-9H-purin-9-yl)methoxy]-1,3-propanediol and 300 ml of a saturated solution of ammonia in methanol was heated at 125° C. in a Parr bomb for 18 hours. The reaction mixture was purified by flash chromatography on silica gel eluting with a methanol dichloromethane gradient (10→40%) to give a light brown solid. This solid was recrystallized from acetonitrile/methanol to yield the title compound as a light brown powder, mp 206°-208° C.

Workup

  1. customThe reaction mixture was purified by flash chromatography on silica gel eluting with a methanol dichloromethane gradient (10→40%)
  2. customto give a light brown solid
  3. customThis solid was recrystallized from acetonitrile/methanol

Sources & evidence

ORD record
ord-0a1c1d3335864af787412d8238537e26
Source dataset
uspto-grants-1987_12
Patent number
US04714701

Reaction notes

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