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

HRID 401119

反応式

HRID 401119 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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]+

後処理

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

出典と根拠

ORDレコード
ord-25cf818e20ae4191a63e0814f4c85397
出典データセット
uspto-grants-2014_06
特許番号
US08741915B2

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