Cesium carbonate → 5-(4-Bromophenyl)pyrimidin-2-amine

HRID 1038011노트

반응식

HRID 1038011 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.O.CCOC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:12][CH:11]=1

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 79599(4-Bromophenyl)boronic acidHCID 2313102-Amino-5-bromopyrimidine

생성물 1

HCID 595113755-(4-Bromophenyl)pyrimidin-2-amine

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 22242641Methanol--water (1/1)용매

실험 절차

A mixture of 5-bromo-pyrimidin-2-ylamine (0.8 g, 4.59 mmol), 4-bromophenyl boronic acid (1 g, 4.97 mmol), tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.259 mmol), cesium carbonate (1.15 g, 3.03 mmol) was stirred in MeOH/H2O (20 ml, 1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200 ml) and water (50 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 85% v/v EtOAc/hexanes yielding product 81 as white solid. (0.7 g, 63%). ESMS (MH, 250).

후처리

  1. temperatureat reflux temperature overnight
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customyielding a residue which
  7. customwas purified on silica gel eluting with 85% v/v EtOAc/hexanes yielding product 81 as white solid

출처 및 근거

ORD 기록
ord-bfa8f93dd33b4e4bab9184efd68cb4e2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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