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

HRID 254181노트

반응식

HRID 254181 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 287995202-Amino-6-phenylpyrimidine-4-carboxylic acid수율 73.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bd6618b5cde74a8da7b403db0ef62d52
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875600B2

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