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Potassium Carbonate → HCID 58495646, 화합물

HRID 1191105
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HRID 1191105 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)[N:3]=1.[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C1(C)C=CC=CC=1.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.C(O)C>[CH:10]1([CH2:9][NH:8][C:4]2[N:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([CH2:21][NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:19])=[CH:23][CH:24]=3)[CH:7]=[CH:6][N:5]=2)[CH2:12][CH2:11]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acidHCID 58495643HCID 58495643, 화합물

생성물 1

HCID 58495646HCID 58495646, 화합물수율 91%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 962Water용매2회
HCID 1140Toluene용매

실험 절차

Slurry 4-chloro-2-(cyclopropylmethyl-amino)-pyrimidine (155 mg, 0.62 mmol), [4-(N-tert-butoxycarbonyl-aminomethyl)phenyl]boronic acid (160 mg, 0.86 mmol), and tetrakis(triphenylphosphine)palladium(0) (36 mg, 0.031 mmol) in toluene (3 mL). Add ethanol (0.5 mL) followed by potassium carbonate (175 mg, 1.24 mmol) dissolved in water (300 μL). Irradiate in microwave (300 watts) at 120° C. for 60 min. Cool to room temperature, pour reaction mixture into water (100 mL) containing 1N NaOH (25 mL) and extract with DCM (3×50 mL). Wash the combined organic extracts with brine, dry over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (12 g) eluting with hexane/EtOAc (4:1 to 3:7 over 30 min; 30 mL/min) to obtain the desired intermediate (200 mg, 90%) as a light yellow solid. MS (ES+) m/z: 355 (M+H)+.

후처리

  1. customIrradiate in microwave (300 watts) at 120° C. for 60 min
  2. additionpour
  3. extractionextract with DCM (3×50 mL)
  4. washWash the combined organic extracts with brine
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel (12 g)
  9. washeluting with hexane/EtOAc (4:1 to 3:7 over 30 min; 30 mL/min)

출처 및 근거

ORD 기록
ord-28a9ded540df4debaa2219fdb67597c6
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680091B2

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