Phosphorus oxychloride → HCID 68853645, compound

HRID 2108344Notes

Reaction equation

HRID 2108344 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([NH2:32])=O)[CH:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.O=P(Cl)(Cl)Cl>C(N(CC)CC)C>[OH:1][CH:2]1[CH:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]#[N:32])[CH:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68944767HCID 68944767, compound

Product 1

HCID 68853645HCID 68853645, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

429 mg of the 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazole-4-carboxamide prepared in Example 5A was dissolved in 5 mL of dimethylformamide(DMF). To this solution was added 0.68 mL of triethylamine followed by chilled (0° C.) POCl3 (0.44 mL). The mixture was stirred and allowed to warm to room temperature. Stirring at room temperature continued 4 hours. The solvent was removed and the residue purified using TLC with a 10:1 dichloromethane:methanol solution to yield 1-{9-[(2R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazole-4-carbonitrile.

Workup

  1. stirringStirring at room temperature
  2. customThe solvent was removed
  3. customthe residue purified

Sources & evidence

ORD record
ord-def723802778471f8eadc49a6691dc88
Source dataset
uspto-grants-2009_04
Patent number
US07514417B2

Reaction notes

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