Benzaldehyde → HCID 178526885, compound

HRID 1640426Notes

Reaction equation

HRID 1640426 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-79f0d4dcb298416ea79e6aa51e3e8caa
Source dataset
uspto-grants-2012_02
Patent number
US08114870B2

Reaction notes

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