Hydrochloric Acid → HCID 135610066, compound

HRID 1271610Notes

Reaction equation

HRID 1271610 reaction equation
[CH3:1][CH2:2][CH2:3][N:4]1[C:37](=[O:38])[N:36]([CH2:39][CH2:40][CH3:41])[C:34](=[O:35])[C:33]2[C:5]1=[N:6]/[C:7](/[N:32]=2)=[C:8]1/[CH:9]=[C:10]([NH:14]C(CC2C=CC(OCC3C=CC=CC=3)=CC=2)=O)[NH:11][N:12]/1[CH3:13].Cl>[OH-].[Na+]>[CH2:39]([N:36]1[C:34](=[O:35])[C:33]2[NH:32][C:7]([C:8]3[N:12]([CH3:13])[N:11]=[C:10]([NH2:14])[CH:9]=3)=[N:6][C:5]=2[N:4]([CH2:3][CH:2]=[CH2:1])[C:37]1=[O:38])[CH:40]=[CH2:41]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178456454HCID 178456454, compound

Product 1

HCID 135610066HCID 135610066, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of the amide intermediate and 30 mL of 2.5 N NaOH is warmed to 70–80° C. for three hours. The clear aqueous solution is cooled and acidified to pH 5 with concentrated HCl. The white precipitate that forms is collected by filtration and washed with H2O to afford the desired 1,3-diallyl-8-(3-amino-1-methylpyrazol-5-yl)xanthine, which is recrystallized from CH3OH. A solution of 4-(benzyloxy)phenylacetic acid (0.196 mmol) in 3 mL of thionyl chloride is stirred at 70° C. for four hours, then excess thionyl chloride removed in a nitrogen stream.

Workup

  1. temperatureis warmed to 70–80° C. for three hours
  2. temperatureThe clear aqueous solution is cooled
  3. filtrationThe white precipitate that forms is collected by filtration
  4. washwashed with H2O

Sources & evidence

ORD record
ord-7408cfc17ab64583af0c687d76b011ad
Source dataset
uspto-grants-2007_04
Patent number
US07205403B2

Reaction notes

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