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

HRID 1966738
Notes
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Reaction equation

HRID 1966738 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-95bf9c7a3a9745f78098884e48821ce2
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420655B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes