Triethylamine → Ethyl 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-(4-quinolinylmethyl)thieno[2,3-d]pyrimidine-5-carboxylate

HRID 900736

反応式

HRID 900736 の反応式
FC(F)(F)C(OC(=O)C(F)(F)F)=O.O[CH:15]([C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]=[CH:39][CH:38]=1)[C:16]1[S:31][C:19]2[N:20]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:21](=[O:26])[N:22]([CH3:25])[C:23](=[O:24])[C:18]=2[C:17]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(N(CC)CC)C>C1COCC1.[Pd]>[CH3:25][N:22]1[C:23](=[O:24])[C:18]2[C:17]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:16]([CH2:15][C:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[N:40]=[CH:39][CH:38]=3)[S:31][C:19]=2[N:20]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:21]1=[O:26]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 5282569Ethyl 1,2,3,4-tetrahydro-6-(hydroxy-4-quinolinylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate

生成物 1

HCID 5282570Ethyl 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-(4-quinolinylmethyl)thieno[2,3-d]pyrimidine-5-carboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Trifluoroacetic anhydride (3.33 ml) was added to a solution of the product of step b) (7.34 g) and triethylamine (6.56 ml) in anhydrous THF (150 ml) at room temperature under nitrogen and the mixture stirred for 15 min. 10% palladium on charcoal (500 mg) was added and the mixture hydrogenated at 1 bar for 20 h. It was filtered through Celite, washing with saturated sodium bicarbonate solution (150 ml) then ethyl acetate (300 ml). The organic material was extracted into ethyl acetate (150 ml), the combined extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with 1:1 ethyl acetate/i-hexane, to give the sub-title compound as a solid (5.90 g).

後処理

  1. waitthe mixture hydrogenated at 1 bar for 20 h
  2. filtrationIt was filtered through Celite
  3. washwashing with saturated sodium bicarbonate solution (150 ml)
  4. extractionThe organic material was extracted into ethyl acetate (150 ml)
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluting with 1:1 ethyl acetate/i-hexane

出典と根拠

ORDレコード
ord-24dd1a48d42240608b7f018ebdea3c53
出典データセット
uspto-grants-2008_04
特許番号
US07361660B2

関連ノート

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