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Sodium Carbonate → HCID 71547536, 화합물

HRID 595073
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HRID 595073 반응식
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[CH:19]1([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)=[O:24])[CH2:21][CH2:20]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:19]1([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:2]3[N:3]=[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]4[CH3:18])[C:5]4[S:11][CH2:10][CH2:9][CH2:8][C:6]=4[N:7]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:21][CH2:20]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 89494611HCID 89494611, 화합물

생성물 1

HCID 71547536HCID 71547536, 화합물수율 80%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 18180031Water 1,2-dimethoxyethane용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-chloro-7,8-dihydro-4-((S)-3-methylmorpholino)-6H-thiopyrano[3,2-d]pyrimidine (150 mg, 0.53 mmol) in DME/H2O (4:1, 10 mL) was added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (175 mg, 0.58 mmol) and Na2CO3 (170 mg, 1.60 mmol) followed by PdCl2(dppf) (15 mg, 0.02 mmol). The resulting mixture was stirred overnight at 70° C. under nitrogen. The solvent was removed under vacuum to give a residue which was partitioned between ethyl acetate and water. The organic layer was separated and dried over anhydrous Na2SO4. The solvent was removed to give crude material which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired productas a white solid (180 mg, 80%).

후처리

  1. customThe solvent was removed under vacuum
  2. customto give a residue which
  3. customwas partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed
  7. customto give crude material which
  8. customwas purified by preparative TLC (DCM/MeOH=20/1)

출처 및 근거

ORD 기록
ord-8887779eb71a466dad350d02c8f908e3
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242993B2

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