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Triphenylphosphine → N-(2,4-dimethylphenyl)-4-((2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methoxy)-N-isobutylbenzenesulfonamide

HRID 1487048
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HRID 1487048 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].O[CH2:25][C:26]1[NH:31][C:30](=[O:32])[NH:29][C:28](=[O:33])[CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:25][C:26]2[NH:31][C:30](=[O:32])[NH:29][C:28](=[O:33])[CH:27]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate2회HCID 971916-(Hydroxymethyl)uracil2회HCID 71543523N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide

생성물 1

HCID 89876095N-(2,4-dimethylphenyl)-4-((2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methoxy)-N-isobutylbenzenesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

A mixture of N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide (33 mg, 0.099 mmol), 6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione (17.1 mg, 0.12 mmol) and triphenylphosphine (26 mg, 0.099 mmol) was dissolved in tetrahydrofuran (THF) (0.6 mL) and treated with diisopropyl diazene-1,2-dicarboxylate (DIAD) (25 uL, 0.13 mmol). The vessel was capped and stirred at 20° C. for 2 days. Additional 6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione (17.1 mg, 0.12 mmol) and diisopropyl diazene-1,2-dicarboxylate (DIAD) (30 uL, 0.156 mmol) were added and reaction stirred for further 18 hours. The reaction was then filtered and purification attempted by mass directed autoprep (ammonium carbonate modifier), but this failed to isolate clean material. Purification successfully achieved by mass directed autoprep (formic acid modifier), to provide the required product, 1.1 mg. LCMS [LCMS1] Rt 1.13 min, m/z (ES+) 458 (M+H).

후처리

  1. customThe vessel was capped
  2. customreaction
  3. stirringstirred for further 18 hours
  4. filtrationThe reaction was then filtered
  5. custompurification
  6. customto isolate clean material
  7. customPurification

출처 및 근거

ORD 기록
ord-ae68993cdfc848a0a6a6dfc2538ee7f6
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09428452B2

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