Water → HCID 178525288, compound

HRID 1955621Notes

Reaction equation

HRID 1955621 reaction equation
[CH:1]1([CH2:7][N:8]2[C:15]([NH2:16])=[C:14]([NH2:17])[C:12](=[O:13])[N:11]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.NC1N(CC2CCCCC2)C(=O)N(CC2CCCCC2)C(=O)C=1N=O.O.[CH:51]([C:53]1[CH:63]=[CH:62][C:56]([CH:57]=[CH:58][C:59]([OH:61])=[O:60])=[CH:55][CH:54]=1)=O>CO.[Pd]>[CH:19]1([CH2:18][N:11]2[C:12](=[O:13])[C:14]3[N:17]=[C:51]([C:53]4[CH:63]=[CH:62][C:56](/[CH:57]=[CH:58]/[C:59]([OH:61])=[O:60])=[CH:55][CH:54]=4)[NH:16][C:15]=3[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:9]2=[O:10])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 222449706-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracilHCID 222449751,3-Bis(cyclohexylmethyl)-5,6-diaminouracil3×

Product 1

HCID 178525288HCID 178525288, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared from 1,3-bis(cyclohexylmethyl)-5,6-diaminouracil by the method of J. Perutmattam, Syn. Commun. 1989, 19:3367-3370. 1,3-Bis(cyclohexylmethyl)-5,6-diaminouracil was freshly prepared by shaking a mixture of 6-amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil (from step (c), 5.00 g, 14.35 mmol) in methanol (250 mL)-water (25 mL) with 10% palladium on carbon (0.50 g) under hydrogen (50 psi) on a Parr shaker for 2 h. The catalyst was filtered off (Celite) and the colorless filtrate was concentrated to 25 mL. 4-Formylcinnamic acid (Aldrich, 2.53 g, 14.35 mmol) was added to this solution of 1,3-bis(cyclohexylmethyl)-5,6-diaminouracil and the resulting yellow mixture was concentrated and the residual yellow solid dried by evaporation of several portions of absolute ethanol. The resulting yellow powder (Schiff base intermediate) was stirred in dimethoxyethane (115 mL) with iodine (4.0 g, 15.7 mequiv) at 60° C. (oil bath) for 20 h. A saturated aqueous solution of sodium thiosulfate was added to the warm reaction mixture until complete decolorization of iodine resulted. The pale yellow precipitate was filtered off, washed with water, and dried at 0.5 Torr to give (E)-4-[1,3 bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]cinnamic acid as a pale yellow powder (6.73 g, 91%), m.p. >300° C. Such samples were further purified by dissolving them in 1N aqueous sodium hydroxide, filtering the resulting hazy solution through Celite, and acidifying the clear filtrate with hydrochloric acid. The resulting precipitate was filtered and washed with water to give title compound as a pale yellow powder, m.p. >300° C.;

Workup

  1. filtrationThe catalyst was filtered off (Celite)
  2. concentrationthe colorless filtrate was concentrated to 25 mL
  3. concentrationthe resulting yellow mixture was concentrated
  4. dry with materialthe residual yellow solid dried by evaporation of several portions of absolute ethanol
  5. stirringThe resulting yellow powder (Schiff base intermediate) was stirred in dimethoxyethane (115 mL) with iodine (4.0 g, 15.7 mequiv) at 60° C. (oil bath) for 20 h
  6. additionA saturated aqueous solution of sodium thiosulfate was added to the warm reaction mixture until complete decolorization of iodine
  7. customresulted
  8. filtrationThe pale yellow precipitate was filtered off
  9. washwashed with water
  10. customdried at 0.5 Torr

Sources & evidence

ORD record
ord-718f1b6289b54e87896402ad05c36726
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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