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 131553

반응식

HRID 131553 반응식
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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

Trifluoroacetic anhydride (3.33 ml) was added to a solution of the product of step d) (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 under reduced pressure. 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). MS(ESI) 452 [M+H]+. δ 1HCDCl3 0.90 (6H,d), 1.37 (3H,t), 2.10-2.16 (1H,m), 3.39 (3H,s), 3.64 (2H,d), 4.45 (2H,q), 4.61 (2H,s), 7.29 (1H,d), 7.60 (1H,t), 7.75 (1H,t), 8.11 (1H,d), 8.16 (1H,d), 8.89 (1H,d)

후처리

  1. waitthe mixture hydrogenated at 1 bar for 20 h
  2. filtrationIt was filtered
  3. washthrough celite washing 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 under reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluting with 1:1 ethyl acetate/i-hexane

출처 및 근거

ORD 기록
ord-b6643247f25c4efc8d48c1138e694c56
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

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