Hydrochloric Acid → 6-(3-Chlorobenzyl)-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 1434540ノート

反応式

HRID 1434540 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26](OC)=O)[CH:22]=[CH:23][CH:24]=1.[H-].[Na+].Cl>C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[CH2:25][C:26]1[NH:17][C:15](=[O:16])[C:3]2[CH:4]=[N:5][N:6]([C:7]3[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:14])[C:2]=2[N:1]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2733544Methyl 2-(3-chlorophenyl)acetateHCID 121505615-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide

生成物 1

HCID 1361755836-(3-Chlorobenzyl)-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

0.1 g (0.43 mmol) of 5-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide (Example 16A) is dissolved under argon in 6 ml of absolute ethanol and 0.24 g (1.3 mmol) of methyl 3-chlorophenylacetate and 0.17 g (4.34 mmol) of 60% sodium hydride (suspension in mineral oil) are added. The reaction mixture is heated to reflux overnight. Cooling to room temperature is followed by acidification with concentrated hydrochloric acid. The sodium chloride precipitated thereby is filtered off. The filtrate is concentrated in vacuo, and the remaining residue is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 59 mg (37% of theory) of the product are obtained as a colourless solid.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customThe sodium chloride precipitated
  4. filtrationthereby is filtered off
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe remaining residue is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  7. custom59 mg (37% of theory) of the product are obtained as a colourless solid

出典と根拠

ORDレコード
ord-58bfcd1382804bfca8aa5c9f1e4c8c9e
出典データセット
uspto-grants-2009_11
特許番号
US07615558B2

反応ノート

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