Ammonia → HCID 10243640, compound

HRID 1885366Notes

Reaction equation

HRID 1885366 reaction equation
[NH3:1].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[CH2:16][C@@H:15]([CH2:17][OH:18])[CH:14]=[CH:13]2)=[C:5](Cl)[N:4]=1>CO>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[CH2:16][C@@H:15]([CH2:17][OH:18])[CH:14]=[CH:13]2)=[C:5]([NH2:1])[N:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11777654(1R,4S)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol

Product 1

HCID 10243640HCID 10243640, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Liquid ammonia is passed into a solution of cis-(±)-2-amino-6-chloro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purine (0.265 g, 1 mmol) in methanol (10 mL) at -80° C. in a bomb. The bomb is sealed and heated at 75° C. for 48 hours. The bomb is cooled to room temperature and the ammonia and methanol are evaporated. The residue is purified by silica gel chromatography using 15:1 chloroform methanol as eluent to give cis-(±)-2,6-diamino-9-[4-(hydroxymethyl)-2-cyclo-penten-1-yl]-9H-purine (0.196 g, 80%). M.pt. 152°-155° C. MS (30 ev, 200° C.): m/e 246 (M+), 229 (M+-17), 216 (M+-30).

Workup

  1. customThe bomb is sealed
  2. temperatureThe bomb is cooled to room temperature
  3. customthe ammonia and methanol are evaporated
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-04bc2087409a45caa590302b58a00f49
Source dataset
uspto-grants-1992_09
Patent number
US05144034

Reaction notes

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