Potassium Carbonate → HCID 10286539, compound

HRID 1355394Notes

Reaction equation

HRID 1355394 reaction equation
Cl[CH2:2][CH2:3][S:4][C:5]1[NH:13][C:12]2[C:11](=[O:14])[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:9](=[O:22])[N:8]([CH3:23])[C:7]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:21][C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:10]1[C:11](=[O:14])[C:12]2[N:13]3[CH2:2][CH2:3][S:4][C:5]3=[N:6][C:7]=2[N:8]([CH3:23])[C:9]1=[O:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69154699HCID 69154699, compound

Product 1

HCID 10286539HCID 10286539, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (R)-8-(2-chloroethylsulfanyl)-1-(5-hydroxyhexyl)-3-methylxanthine (76 mg, 0.21 mmol) and potassium carbonate (58 mg, 0.42 mmol) in acetonitrile (15 ml) was stirred at 80° C. for 2 hours. After concentrating under reduced pressure, the residue was purified by column chromatography eluting with ethyl acetate-hexane (1:1) to provide (R)-6,7-dihydro-3-(5-hydroxyhexyl)-1-methyl-thiazolo[2,3-f]purine-2,4(1H,3H)-dione (CT 13421) (22 mg, 32% yield) as a white powder.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was purified by column chromatography
  3. washeluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-252ded3896d046b8820ec5d3a1cce5f8
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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