Sodium Carbonate → HCID 44197933, 화합물

HRID 1970955노트

반응식

HRID 1970955 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:11]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)[CH2:27][CH2:26]1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.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>[C:14]([C:12]1[CH:13]=[C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:35]3[CH:34]=[CH:33][C:32]([CH2:31][N:28]4[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]4)=[CH:37][CH:36]=3)[CH:3]=2)[N:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:11]=1)([CH3:17])([CH3:16])[CH3:15]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 454965984-((4-Methylpiperazin-1-yl)methyl)phenylboronic acidHCID 68773882HCID 68773882, 화합물

생성물 1

HCID 44197933HCID 44197933, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 20074477Dimethoxyethane ethanol용매

실험 절차

To a solution of 4-(5-bromo-pyridin-3-yl)-6-tert-butyl-2-pyridin-2-yl-pyrimidine (1 eq, 200 mg, 0.542 mmol) in EtOH/DME (2 ml, 1:1) is added 4-(4-methyl-piperazin-1-ylmethyl)-phenyl-boronic acid (1.1 eq, 174 mg, 0.596 mmol), aqueous Na2CO3 solution (2 M, 3 eq, 0.812 ml, 1.63 mmol) and Pd(PPh3)4 (0.05 eq, 31 mg, 0.027 mmol). The resulting mixture is heated using microwave radiation for 20 min at 140° C. The mixture is filtered, washed with DCM and concentrated in vacuo. The residue is partitioned between sat. aqueous NaHCO3 solution and DCM and the organic layer is washed with brine, dried (MgSO4) concentrated under reduced pressure. The resulting residue is purified by reverse phase chromatography yielding the title compound; [M+H]+=479. 1H NMR (CDCl3, 400 MHz): 9.26 (d, 1H), 8.95 (d, 1H), 8.87 (m, 1H), 8.66 (t, 1H), 8.62 (m, 1H), 7.88 (td, 1H), 7.77 (s, 1H), 7.64 (d, 2H), 7.47 (d, 2H), 7.41 (ddd, 1H), 3.58 (s, 2H), 2.60-2.43 (m, 8H), 2.32 (s, 3H), 1.51 (s, 9H).

후처리

  1. temperatureThe resulting mixture is heated
  2. customfor 20 min
  3. customat 140° C
  4. filtrationThe mixture is filtered
  5. washwashed with DCM
  6. concentrationconcentrated in vacuo
  7. customThe residue is partitioned between sat. aqueous NaHCO3 solution and DCM
  8. washthe organic layer is washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue is purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-c23913768ebf4755887712dd705babaa
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431578B2

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