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Sodium Carbonate → Tert-butyl 4-(2-aminopyrimidin-5-yl)benzoate

HRID 1257818
Notes
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Reaction equation

HRID 1257818 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[C:15]([O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>O.C(O)C.C1(C)C=CC=CC=1.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>[NH2:14][C:11]1[N:10]=[CH:9][C:8]([C:25]2[CH:26]=[CH:27][C:22]([C:20]([O:19][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:21])=[CH:23][CH:24]=2)=[CH:13][N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 2773301(4-((Tert-butoxy)carbonyl)phenyl)boronic acid

Product 1

HCID 67225251Tert-butyl 4-(2-aminopyrimidin-5-yl)benzoateYield 86.6%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Sodium carbonate (0.636 g, 6.0 mmol) in water (2.0 mL) was added to a mixture of 5-bromopyrimidin-2-amine (0.348 g, 2.0 mmol), [4-(tert-butoxycarbonyl)phenyl]boronic acid (0.533 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in ethanol (3 mL) and toluene (3 mL). The mixture was heated at 120° C. for 3 h. After cooling to RT, the mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (470 mg, 86.6%) which was directly used in next step. LCMS: (M+H)=272.1.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8cdfd873ee8a44ecaacbb4a34b35256d
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461330B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes