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Sodium Carbonate → 5-(4-Tert-butylamino-3-nitro-phenyl)-4-methoxy-pyrimidin-2-ylamine

HRID 1966738
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HRID 1966738 반응식
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:7]=1[N+:21]([O-:23])=[O:22])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[N:30]=[C:29]([O:31][CH3:32])[C:28](Br)=[CH:27][N:26]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=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:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:28]2[C:29]([O:31][CH3:32])=[N:30][C:25]([NH2:24])=[N:26][CH:27]=2)=[CH:8][C:7]=1[N+:21]([O-:23])=[O:22])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 450369372-Amino-5-bromo-4-methoxypyrimidineHCID 53217134N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

생성물 1

HCID 585420425-(4-Tert-butylamino-3-nitro-phenyl)-4-methoxy-pyrimidin-2-ylamine수율 86.1%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To a vial is added tert-butyl-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-amine (300 mg, 0.937 mmol), 2-amino-5-bromo-4-methoxypyrimidine (215 mg, 1.054 mmol) and 2M Na2CO3 (2 mL, 4 mmol) in DMF (10 mL), followed by the addition of tetrakis(triphenylphosphine)palladium(0) (108 mg, 0.093 mmol). The vial is sealed under Argon gas. The reaction mixture is stirred at 110° C. for 18 hours. The reaction mixture is diluted with EtOAc and washed with water. The organic layer is separated, washed with brine, dried under Na2SO4, filtered and concentrated. The residue is loaded onto a silica gel column. The column is eluted with 0-5% MeOH/CH2Cl2. The product fractions are collected and concentrated to afford 5-(4-tert-butylamino-3-nitro-phenyl)-4-methoxy-pyrimidin-2-ylamine (256 mg, 86%) as a red solid. LCMS (ESMS): m/z 318.72 (M++1)

후처리

  1. customThe vial is sealed under Argon gas
  2. washwashed with water
  3. customThe organic layer is separated
  4. washwashed with brine
  5. customdried under Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe column is eluted with 0-5% MeOH/CH2Cl2
  9. customThe product fractions are collected
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-95bf9c7a3a9745f78098884e48821ce2
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08420655B2

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