Sodium Carbonate → 5-[6-(2-Fluoro-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-pyridin-2-ylamine

HRID 1043802노트

반응식

HRID 1043802 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:3]=1.[F:21][C:22]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[CH:24][N:23]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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].ClCCl>[F:21][C:22]1[C:27]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:5]=[C:4]([C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)[CH:3]=2)=[CH:26][CH:25]=[CH:24][N:23]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 120670632-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 595075305-(6-Chloro-2-morpholin-4-ylpyrimidin-4-yl)pyridin-2-ylamine

생성물 1

HCID 595074715-[6-(2-Fluoro-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-pyridin-2-ylamine

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

To a solution of 5-(6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)pyridin-2-ylamine, prepared as in Example 2, (252 mg, 0.87 mmol) and 2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (183 mg, 1.30 mmol) in DME (4 mL) was added an aqueous solution of Na2CO3 (2 M, 1 mL), followed by dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane (71 mg, 0.087 mmol). The mixture was heated in a microwave for 20 min at 120° C. The aqueous phase was separated from DME, and extracted with EtOAc. The combined organic phases were washed with brine, dried, filtered, and concentrated to give crude desired product which was carried on to the next step without further purification. LC/MS (m/z): 353.3 (MH+), 1.84 minutes.

후처리

  1. customThe aqueous phase was separated from DME
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7a8c32acaa594ee2904fea9181477aeb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563549B2

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