HCID 178525288, compound → HCID 178525291, compound

HRID 1955634Notes

Reaction equation

HRID 1955634 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[N:14]=[C:13]([C:18]4[CH:28]=[CH:27][C:21](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[CH:20][CH:19]=4)[NH:12][C:11]=3[N:10]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:9]2=[O:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CN(C=O)C>[CH:1]1([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[N:14]=[C:13]([C:18]4[CH:19]=[CH:20][C:21]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:27][CH:28]=4)[NH:12][C:11]=3[N:10]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:9]2=[O:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 178525288HCID 178525288, compound

Product 1

HCID 178525291HCID 178525291, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

(E)-4-[1,3 Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]cinnamic acid (from step (d) example 1, 560 mg, 1.13 mmol) was shaken with 10% palladium on carbon (500 mg) in DMF (100 mL) under hydrogen (30 psi) in a Parr apparatus for 6 h. Catalyst was filtered off (Celite) and volatiles evaporated in vacuo. The residual oil was solidified from DMF, filtered, dissolved in 1N sodium hydroxide, and then reprecipitated by addition of excess 1N hydrochloric acid. Such a sample was filtered, washed with water and dried to give title compound as a white powder, m.p. >300° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. filtrationCatalyst was filtered off (Celite)
  2. customvolatiles evaporated in vacuo
  3. filtrationfiltered
  4. dissolutiondissolved in 1N sodium hydroxide
  5. customreprecipitated by addition of excess 1N hydrochloric acid
  6. filtrationSuch a sample was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-157457a175e4493bae2d397e2935c99c
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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