Potassium Carbonate → HCID 86696631, compound

HRID 1468609Notes

Reaction equation

HRID 1468609 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([NH2:12])=[C:4]([Cl:13])[N:3]=1.[C:14]([O-])([O-])=[O:15].[K+].[K+].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O>C(#N)C>[NH2:1][C:2]1[N:7]=[C:6]2[C:5]([NH:12][C:14](=[O:15])[N:8]2[CH2:9][CH2:10][OH:11])=[C:4]([Cl:13])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 821294-Nitrophenyl chloroformateHCID 18706827HCID 18706827, compound

Product 1

HCID 86696631HCID 86696631, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-[(2,5-diamino-6-chloro-pyrimidin-4-yl)amino]ethanol obtained in step 1 (10.0 g, 49.26 mmol) in acetonitrile (400 ml) were cooled to 0° C. To this reaction mixture K2CO3 (20.39 gm, 147.7 mmol) and 4-nitrophenyl chloroformate (19.8 g, 98.52 mmol)was added and stirred at 25-27° C. for 24 hours. This reaction mixture was filtered and washed with acetonitrile (300 ml) and diethyl ether (300 ml) respectively. Solid obtained was dried to obtain crude 2-amino-6-chloro-9-(2-hydroxyethyl)-7H-purin-8-one as a yellow solid. Small amount of crude material was purified by column chromatography to obtain pure product.

Workup

  1. filtrationThis reaction mixture was filtered
  2. washwashed with acetonitrile (300 ml) and diethyl ether (300 ml) respectively
  3. customSolid obtained
  4. customwas dried

Sources & evidence

ORD record
ord-3f2f60b8fefc4f1a91db87f7d8316030
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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