Phenylboronic Acid → 2-Amino-6-phenylpyrimidine-4-carboxylic acid

HRID 254181ノート

反応式

HRID 254181 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

参加物

5

反応物 3

HCID 66827Phenylboronic AcidHCID 239687Methyl 2-amino-6-chloropyrimidine-4-carboxylateHCID 516892Sodium Bicarbonate

生成物 1

HCID 287995202-Amino-6-phenylpyrimidine-4-carboxylic acid収率 73.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

A solution of methyl 2-amino-6-chloropyrimidine-4-carboxylate (0.2 g, 1.07 mmol) and phenylboronic acid (0.16 g, 1.3 mmol) in THF (10 mL) was treated with saturated aqueous NaHCO3 (1.6 mL). Nitrogen was bubbled through the solution for 5 min then tetrakis(triphenylphosphine)palladium(0) (0.04 g) was added and the mixture refluxed under nitrogen overnight. The mixture was treated with aqueous LiOH (1-M, 1 mL), heated at 90° C. for 2 h, concentrated in vacuo and partitioned between ethyl acetate and water. The aqueous layer was acidified to pH 1 with 2-N HCl, the resulting suspension centrifuged, the liquors decanted and the resulting solid dried to give the title compound (0.17 g, 72%) as a white powder which was used directly in the next step without further purification; M/Z 216 (M+H)+; retention time 1.60 min (Method AM).

後処理

  1. customNitrogen was bubbled through the solution for 5 min
  2. additiontetrakis(triphenylphosphine)palladium(0) (0.04 g) was added
  3. temperaturethe mixture refluxed under nitrogen overnight
  4. additionThe mixture was treated with aqueous LiOH (1-M, 1 mL)
  5. concentrationconcentrated in vacuo
  6. custompartitioned between ethyl acetate and water
  7. customthe liquors decanted
  8. customthe resulting solid dried

出典と根拠

ORDレコード
ord-bd6618b5cde74a8da7b403db0ef62d52
出典データセット
uspto-grants-2011_01
特許番号
US07875600B2

反応ノート

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