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

HRID 401123ノート

反応式

HRID 401123 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:2]=1.[N:15]1[NH:16][N:17]=[N:18][C:19]=1[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.[NH2:28][C:29]([NH2:31])=[O:30].Cl>CCO>[N:15]1[NH:16][N:17]=[N:18][C:19]=1[C:20]1[CH:27]=[CH:26][C:23]([CH:24]2[C:8]([C:9]3[CH:13]=[CH:12][S:11][CH:10]=3)=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:31][C:29](=[O:30])[NH:28]2)=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehydeHCID 610560411-(Pyridin-3-yl)-2-(thiophen-3-yl)ethanone2 回

生成物 1

HCID 668259114-(4-(2H-tetrazol-5-yl)phenyl)-6-(pyridin-3-yl)-5-(thiophen-3-yl)-3,4-dihydropyrimidin-2(1H)-one収率 35.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-(pyridin-3-yl)-2-(thiophen-3-yl)ethanone (Intermediate 56) (80 mg, 0.39 mmol), 4-(2H-tetrazol-5-yl)benzaldehyde (300 mg), urea (120 mg, 2.0 mmol) and conc. HCl (0.5 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 166 (56 mg, yield 35%) as yellow solid. 1H NMR (CD3OD 400 MHz): δ 8.71-8.61 (m, 2H), 8.30 (d, J=8.0 Hz, 1H), 8.04 (d, J=8.0 Hz, 2H), 7.85-7.78 (m, 1H), 7.65 (d, J=8.0 Hz, 2H), 7.22 (dd, J=2.8 Hz, J=4.8 Hz, 1H), 6.89 (dd, J=1.6 Hz, J=3.2 Hz, 1H), 6.56 (dd, J=1.2 Hz, J=5.2 Hz, 1H), 5.50 (s, 1H). MS (ESI): m/z 402.3 [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-a2deef09ad7946649472cfc592d1ee24
出典データセット
uspto-grants-2014_06
特許番号
US08741915B2

反応ノート

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