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

HRID 401119

반응식

HRID 401119 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehydeHCID 43289002-Phenyl-1-pyridin-3-yl-ethanone2회

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]+

후처리

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

출처 및 근거

ORD 기록
ord-25cf818e20ae4191a63e0814f4c85397
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741915B2

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