Triphenylphosphine → Tert-butyl 4-(5-(3-(4-fluorophenyl)oxetan-3-yl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 1498869

反応式

HRID 1498869 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:14]=[N:15][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:17][CH:18]=2)([CH2:11][OH:12])[CH2:9]O)=[CH:4][CH:3]=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>C1COCC1.CN(C([S-])=S)C.CN(C([S-])=S)C.[Zn+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]3[CH:14]=[N:15][C:16]([N:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:23][CH2:24]4)=[N:17][CH:18]=3)[CH2:9][O:12][CH2:11]2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 118023378Tert-butyl 4-(5-(2-(4-fluorophenyl)-1,3-dihydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 118023292Tert-butyl 4-(5-(3-(4-fluorophenyl)oxetan-3-yl)pyrimidin-2-yl)piperazine-1-carboxylate収率 6%

試薬・触媒・溶媒 2

HCID 8722Ziram触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

A mixture of tert-butyl 4-(5-(2-(4-fluorophenyl)-1,3-dihydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate (650 mg, 1.5 mmol), triphenylphosphine (470 mg, 1.8 mmol), diisopropyl azodicarboxylate (360 mg, 1.8 mmol) and ziram (500 mg, 1.8 mmol) in THF (50 mL) was heated at 40° C. overnight under N2 and concentrated. The residue was diluted with EtOAc (40 mL), washed with water (50 mL*2) and brine, dried over Na2SO4 and concentrated. The residue was purified by Prep-HPLC to give the desired product (35 mg, yield 6%) as a white solid. MS (ES+) C22H27FN4O3 requires: 414. found 359 [M+H−56]+; purity: 93% (UV214).

後処理

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (40 mL)
  3. washwashed with water (50 mL*2) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by Prep-HPLC

出典と根拠

ORDレコード
ord-2de6eec56cbc40fab365c834fa35452f
出典データセット
uspto-grants-2015_12
特許番号
US09200002B2

関連ノート

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