Hydrochloric Acid → 4-(4-(2H-tetrazol-5-yl)phenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 924910Notes

Reaction equation

HRID 924910 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:16]1[NH:17][N:18]=[N:19][C:20]=1[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>CCO>[N:16]1[NH:17][N:18]=[N:19][C:20]=1[C:21]1[CH:28]=[CH:27][C:24]([CH:25]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:32][C:30](=[O:31])[NH:29]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Product 1

HCID 569615144-(4-(2H-tetrazol-5-yl)phenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-oneYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-diphenylethanone (150 mg, 0.76 mmol), 4-(2H-tetrazol-5-yl)benzaldehyde (400 mg), urea (230 mg, 3.8 mmol) and conc. HCl (0.5 mL) in EtOH (5 mL) was refluxed under N2 overnight. Solvent was removed in vacuo and purified by prep-HPLC (0.1% TFA as additive) to give Compound 164 (45 mg, yield 15%) as off-white solid. 1H NMR DMSO-d6 400 MHz): δ 8.75-8.68 (m, 1H), 8.00 (d, J=8.0 Hz, 2H), 7.65-7.60 (m, 1H), 7.55 (d, J=8.0 Hz, 2H), 7.28-7.16 (m, 5H), 7.06-6.96 (m, 3H), 6.84-6.78 (m, 2H), 5.28 (s, 1H). MS (ESI): m/z 395.5 [M+1]+.

Workup

  1. temperaturewas refluxed under N2 overnight
  2. customSolvent was removed in vacuo
  3. custompurified by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-29f8020ed8bc4c1ebc02ecd8107e50e4
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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