Triphenylphosphine → HCID 59484895、化合物

HRID 1408407ノート

反応式

HRID 1408407 の反応式
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)=[N:13]2)=[N:6][CH:7]=1.[O:28]1CCC[CH2:30][CH:29]1OCCO.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>ClCCl.C1COCC1>[OH:28][CH2:29][CH2:30][O:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)=[N:13]2)=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 59438049HCID 59438049、化合物

生成物 1

HCID 59484895HCID 59484895、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

252 mg of 2-[3-(5-hydroxypyrimidin-2-yl)benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one (0.7 mmol) are suspended in abs. THF under a protective-gas atmosphere in a 25 ml three-necked flask, 0.19 ml of 2-(tetrahydropyran-2-yloxy)ethanol (1.4 mmol) and 367 mg of triphenylphosphine (1.4 mmol) are added, and the mixture is stirred at RT for 30 min. 275 μl of diisopropyl azodicarboxylate (1.4 mmol) are subsequently added dropwise, and the reaction mixture is stirred at RT for a further 2 h. For work-up, the reaction mixture is diluted with 20 ml of dichloromethane, washed with 10 ml of water, dried over sodium sulfate, evaporated to dryness and purified by chromatography. (silica gel: MTB ether->DCM->DCM: 30% of MeOH). The THP-protected product is stirred at RT for 20 h in 5 ml of 4 N HCl in dioxane. The reaction solution is evaporated to dryness and crystallised from methanol/diethyl ether, giving “A294”; ESI 405; m.p. 182-3° C.

後処理

  1. stirringthe reaction mixture is stirred at RT for a further 2 h
  2. washwashed with 10 ml of water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. custompurified by chromatography
  6. stirringThe THP-protected product is stirred at RT for 20 h in 5 ml of 4 N HCl in dioxane
  7. customThe reaction solution is evaporated to dryness
  8. customcrystallised from methanol/diethyl ether
  9. customgiving “A294”

出典と根拠

ORDレコード
ord-a19635382def47d1a5dfc1e53ba65832
出典データセット
uspto-grants-2014_12
特許番号
US08921357B2

反応ノート

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