2-Propenoic acid, 3-(4-formylphenyl)- → HCID 178525292, compound

HRID 1955645Notes

Reaction equation

HRID 1955645 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[S:15])[N:5]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:4](=[O:23])[C:3]=1[N:24]=O.C1(CN2C(N)=C(N)C(=O)N(CC3CCCCC3)C2=S)CCCCC1.[CH:50]([C:52]1[CH:62]=[CH:61][C:55]([CH:56]=[CH:57][C:58]([OH:60])=[O:59])=[CH:54][CH:53]=1)=O>C(O)C>[CH:17]1([CH2:16][N:5]2[C:4](=[O:23])[C:3]3[N:24]=[C:50]([C:52]4[CH:62]=[CH:61][C:55](/[CH:56]=[CH:57]/[C:58]([OH:60])=[O:59])=[CH:54][CH:53]=4)[NH:1][C:2]=3[N:7]([CH2:8][CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:6]2=[S:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 19071314HCID 19071314, compoundHCID 19071334HCID 19071334, compound

Product 1

HCID 178525292HCID 178525292, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the manner of step (d) of example 8, 6-amino-1,3-bis(cyclohexylmethyl-1,2-dihydro-5-nitroso-2-thioxo-4(3H)-pyrimidinone (from step (c), 3.00 g, 8.20 mmol) was reduced to 1,3-bis(cyclohexylmethyl)-5,6-diamino-1,2-dihydro-2-thioxo-4(3H)-pyrimidinone, which was then combined with 4-formylcinnamic acid (Aldrich, 1.44 g, 8.20 mmol) in ethanol (150 mL). The resulting yellow mixture was dried by evaporation of several portions of absolute ethanol, and the residual yellow powder (Schiff base intermediate) was heated at reflux in nitrobenzene (150 mL) until no more water distilled off. The reaction mixture was then cooled to ambient temperature, and stirred in ether (200 ml). The resulting pale yellow precipitate was filtered off, washed with hot ethanol (100 mL), followed by ether (100 mL), and dried under vacuum at 110° C. to afford (E)-4-(1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-6-oxo-2-thioxo-9H-purin-8-yl)cinnamic acid as a yellow powder (2.32 g, 65%), m.p. >300° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. dry with materialThe resulting yellow mixture was dried by evaporation of several portions of absolute ethanol
  2. temperaturethe residual yellow powder (Schiff base intermediate) was heated
  3. temperatureat reflux in nitrobenzene (150 mL) until no more water
  4. distillationdistilled off
  5. filtrationThe resulting pale yellow precipitate was filtered off
  6. washwashed with hot ethanol (100 mL)
  7. customdried under vacuum at 110° C.

Sources & evidence

ORD record
ord-bc4a276d9a5e4b5796e5c23cc4c2c79d
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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