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

HRID 924908Notes

Reaction equation

HRID 924908 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[C:14]1([CH2:20][C:21]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>CCO>[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]2[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:21]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:32][C:30](=[O:31])[NH:29]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehydeHCID 43289002-Phenyl-1-pyridin-3-yl-ethanone2×

Product 1

HCID 513470414-(4-(2H-tetrazol-5-yl)phenyl)-5-phenyl-6-(pyridin-3-yl)-3,4-dihydropyrimidin-2(1H)-oneYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(2H-tetrazol-5-yl)benzaldehyde (106 mg), 2-phenyl-1-(pyridin-3-yl)ethanone (Intermediate 31) (100 mg, 0.51 mmol), urea (120 mg, 2.0 mmol) and conc. HCl (0.2 mL) in EtOH (5 mL) was refluxed under N2 overnight. The mixture was concentrated under reduced pressure and purified by prep-HPLC (0.1% TFA as additive) to give Compound 162 (50 mg, 2-step yield 25%). 1H NMR (DMSO-d6 400 MHz): δ 8.97 (s, 1H), 8.52 (d, J=4.4 Hz, 1H), 8.89 (s, 1H), 8.05-7.97 (m, 2H), 7.85 (d, J=8.0 Hz, 1H), 7.69 (s, 1H), 7.57 (d, J=8.0 Hz, 2H), 7.49-7.44 (m, 1H), 7.07-7.00 (m, 3H), 6.89-6.85 (m, 2H), 5.38 (s, 1H). MS (ESI): m/z 396.4 [M+1]+

Workup

  1. temperaturewas refluxed under N2 overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompurified by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-934ead5c1ee04715871ee5e547b61508
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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