Sodium Methoxide → Methyl 3-{4-hydroxy-6-oxo-2-[(E)-2-phenylethenyl]-1,6-dihydro-5-pyrimidinyl}propanoate

HRID 657111

反応式

HRID 657111 の反応式
[CH:1]([C:13]([O:15]C)=O)([C:9]([O:11]C)=O)[CH2:2][CH2:3][C:4]([O:6][CH2:7]C)=[O:5].[C:17]1(/[CH:23]=[CH:24]/[C:25](=[NH:27])[NH2:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[O-].[Na+]>CO>[OH:15][C:13]1[N:26]=[C:25](/[CH:24]=[CH:23]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:27][C:9](=[O:11])[C:1]=1[CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 10942334Sodium MethoxideHCID 130424803-Ethyl 1,1-dimethyl 1,1,3-propanetricarboxylateHCID 14668188Cinnamimidamide

生成物 1

HCID 68992584Methyl 3-{4-hydroxy-6-oxo-2-[(E)-2-phenylethenyl]-1,6-dihydro-5-pyrimidinyl}propanoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

3-Ethyl 1,1-dimethyl 1,1,3-propanetricarboxylate (23.8 g; 103 mmol) and (2E)-3-phenyl-2-propenimidamide (10.0 g; 68.4 mmol) were combined in MeOH (400 mL), treated with NaOMe in MeOH (31.0 g; 143 mmol) and the solution was stirred at room temperature for 2 days. The solution turned dark, and a dark green solid was filtered off. The solution was concentrated under vacuum, diluted with water, acidified to pH 2 with 6N HCl and the resulting yellow precipitate was filtered off. The aqueous mother liquor was extracted with EtOAc. During the extraction more yellow precipitate formed and was collected. The combined yellow solids were dried under vacuum and used without further purification (12.1 g, 59%).

後処理

  1. filtrationa dark green solid was filtered off
  2. concentrationThe solution was concentrated under vacuum
  3. additiondiluted with water
  4. filtrationthe resulting yellow precipitate was filtered off
  5. extractionThe aqueous mother liquor was extracted with EtOAc
  6. extractionDuring the extraction more yellow precipitate
  7. customformed
  8. customwas collected
  9. customThe combined yellow solids were dried under vacuum
  10. customused without further purification (12.1 g, 59%)

出典と根拠

ORDレコード
ord-71e87ad73dd84ac9a75668d9799b6a0f
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

関連ノート

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