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

HRID 2233213ノート

反応式

HRID 2233213 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][CH3:8])=[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(N(CC)CC)C.C[O-].[Na+].CO>CCO>[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][CH2:7][CH3:8])=[O:5]

参加物

7

反応物 5

HCID 887Methanol2 回HCID 8471TriethylamineHCID 10942334Sodium Methoxide2 回HCID 130424803-Ethyl 1,1-dimethyl 1,1,3-propanetricarboxylateHCID 14668188Cinnamimidamide

生成物 1

HCID 67548308Ethyl 3-{4-hydroxy-6-oxo-2-[(E)-2-phenylethenyl]-1,6-dihydro-5-pyrimidinyl}propanoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3-Ethyl 1,1-dimethyl 1,1,3-propanetricarboxylate (1.65 g, 7.11 mmol) and (2E)-3-phenyl-2-propenimidamide (1.04 g, 7.11 mmol) were combined in EtOH (36 mL). Triethylamine (1.98 mL, 14.2 mmol) was added and the solution was heated at reflux for 3 h with no change based on LCMS. The solution was cooled to room temperature and treated with NaOMe in MeOH (1.0 mL, 5.33 mmol, 25% wt solution) and the solution was refluxed for an additional 4 h. Another portion of NaOMe in MeOH (1.0 mL, 5.33 mmol, 25% wt solution) was added and the solution was refluxed for 16 h. After this time, a yellow precipitate had formed which was filtered off. The mother liquor was acidified to pH2 with 1N HCl, and the solution was concentrated under vacuum. The resulting material was combined with the yellow solid and used without further purification.

後処理

  1. temperaturethe solution was heated
  2. temperatureat reflux for 3 h with no change
  3. temperaturethe solution was refluxed for an additional 4 h
  4. temperaturethe solution was refluxed for 16 h
  5. customAfter this time, a yellow precipitate had formed which
  6. filtrationwas filtered off
  7. concentrationthe solution was concentrated under vacuum
  8. customused without further purification

出典と根拠

ORDレコード
ord-d00b5518438f4d2a9aa5e8bfe439c582
出典データセット
uspto-grants-2010_05
特許番号
US07709483B2

反応ノート

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