Benzaldehyde → HCID 178526885, compound

HRID 229328Notes

Reaction equation

HRID 229328 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([OH:12])[N:3]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1.CO>C(OCC)C>[N+:9]([C:5]1[C:6]([OH:8])=[N:7][C:2](/[CH:1]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:3][C:4]=1[OH:12])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 8082PiperidineHCID 178433493HCID 178433493, compound

Product 1

HCID 178526885HCID 178526885, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-methyl-5-nitropyrimidine-4,6-diol (4.7 g, 27.5 mmol) and benzaldehyde (42 mL, 414 mmol) was treated with piperidine (21.3 mL, 215.3 mmol). The reaction mixture was heated to 90° C. for 2 hrs. The temperature was then increased to 120° C. for 30 min. After cooling the reaction mixture to ambient, methanol (10 mL) and diethyl ether (200 mL) were added sequentially. The resulting solid was collected by filtration and washed with 5% aqueous hydrochloric acid to give 5-nitro-2-[(E)-2-phenylvinyl]pyrimidine-4,6-diol (4.5 g). 1H NMR (400 MHz, DMSO-d6): δ 8.15 (d, 1H, J=16.4 Hz), 7.15 (m, 2H), 7.54 (m, 3H), 6.81 (d, 1H, J=16.4 Hz). MS (m/z) 260 (M+1).

Workup

  1. temperatureThe temperature was then increased to 120° C. for 30 min
  2. additionwere added sequentially
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with 5% aqueous hydrochloric acid

Sources & evidence

ORD record
ord-c47d854b77324958bc884afeafa69622
Source dataset
uspto-grants-2009_07
Patent number
US07563787B2

Reaction notes

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