3-Chloro-4-pyridineboronic acid → 5-(3-Chloro-pyridin-4-yl)-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine

HRID 875944

반응식

HRID 875944 반응식
Br[C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1B(O)O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1

참가 물질

5

반응물 2

HCID 38618773-Chloro-4-pyridineboronic acidHCID 582996735-Bromo-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine

생성물 1

HCID 583000215-(3-Chloro-pyridin-4-yl)-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine수율 98%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
130 °C

실험 절차

A mixture of compound 33 (2.03 g, 7.43 mmol), 3-chloropyridin-4-ylboronic acid (3.51 g, 22.3 mmol), and Pd(PPh3)2Cl2 (0.522 g, 0.743 mmol) in dioxane (44 ml) in a pressure vessel was purged with N2 for 20 minutes and to this mixture was added aq. Na2CO3 (1 M, 22 mL) by syringe. The reaction was further purged with N2 for another 20 minutes and then heated to 130° C. for 12 hours. DCM was added to the reaction and the mixture was washed with water and brine. The organic layer was dried with sodium sulfate and concentrated to provide compound 34 (2.07 g, crude, 98%) which was used in the next reaction without further purification. LCMS-ESI (POS), M/Z, M+1: Found 306.1, Calculated 306.1.

후처리

  1. customwas purged with N2 for 20 minutes and to this mixture
  2. additionwas added aq. Na2CO3 (1 M, 22 mL) by syringe
  3. customThe reaction was further purged with N2 for another 20 minutes
  4. additionDCM was added to the reaction
  5. washthe mixture was washed with water and brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4ffe5995e4ef4227aa7e7f5e8e681efe
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

연결된 노트

불러오는 중…