Triphenylphosphine → 2-(((5-Chloropyrido[3,4-b]pyrazin-2-yl)oxy)methyl)-5-methyloxazole

HRID 627717ノート

反応式

HRID 627717 の反応式
[Cl:1][C:2]1[C:7]2=[N:8][CH:9]=[C:10]([OH:12])[N:11]=[C:6]2[CH:5]=[CH:4][N:3]=1.[CH3:13][C:14]1[O:18][C:17]([CH2:19]O)=[N:16][CH:15]=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>[Cl:1][C:2]1[C:7]2=[N:8][CH:9]=[C:10]([O:12][CH2:19][C:17]3[O:18][C:14]([CH3:13])=[CH:15][N:16]=3)[N:11]=[C:6]2[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22081028(5-Methyl-1,3-oxazol-2-yl)methanolHCID 178516729HCID 178516729、化合物

生成物 1

HCID 867281542-(((5-Chloropyrido[3,4-b]pyrazin-2-yl)oxy)methyl)-5-methyloxazole収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-chloropyrido[3,4-b]pyrazin-2-ol (200 mg, 1.1 mmol) and (5-methyloxazol-2-yl)methanol (187 mg, 1.6 mmol) in tetrahydrofuran (5 mL) was added triphenylphosphine (433 mg, 1.6 mmol). The reaction mixture was cooled to 0° C. and diisopropyl azodicarboxylate (0.33 mL, 1.6 mmol) was added slowly. The reaction was stirred at 0° C. for 1 hour, and then allowed to warm to ambient temperature overnight. After 16 hours, the reaction was quenched with water and extracted into ethyl acetate. The organic layer was concentrated, and the crude product was purified by column chromatography, eluting with 20-80% (3:1 ethyl acetate/ethanol) in heptane. The less-polar isomer was isolated to provide the title compound (120 mg, 0.43 mmol, 79% yield) as a white solid. LC/MS (ESI+) m/z: 277.0 (M+H+).

後処理

  1. temperatureto warm to ambient temperature overnight
  2. waitAfter 16 hours
  3. customthe reaction was quenched with water
  4. extractionextracted into ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe crude product was purified by column chromatography
  7. washeluting with 20-80% (3:1 ethyl acetate/ethanol) in heptane
  8. customThe less-polar isomer was isolated

出典と根拠

ORDレコード
ord-754229f9b61c402689b1bccf2746d67d
出典データセット
uspto-grants-2016_04
特許番号
US09309263B2

反応ノート

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