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Phenylboronic Acid → 1-tert-butyl-5-(2-phenylpyrimidin-4-yl)-1H-pyrazole-3-carboxamide

HRID 925413
Notes
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Reaction equation

HRID 925413 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12](SC)[N:11]=2)=[CH:8][C:7]([C:18]([NH2:20])=[O:19])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.S1C=CC=C1C([O-])=O.[Cu+2].S1C=CC=C1C([O-])=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]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:11]=2)=[CH:8][C:7]([C:18]([NH2:20])=[O:19])=[N:6]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 665582581-tert-butyl-5-[2-(methylsulfanyl)pyrimidin-4-yl]-1H-pyrazole-3-carboxamide

Product 1

HCID 665582631-tert-butyl-5-(2-phenylpyrimidin-4-yl)-1H-pyrazole-3-carboxamideYield 23%

Reagents, catalysts & solvents 3

HCID 15171005Copper thiophene-2-carboxylateCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
130 °C

Procedure

50 mg (0.172 mmol) of 1-tert-butyl-5-[2-(methylsulfanyl)pyrimidin-4-yl]-1H-pyrazole-3-carboxamide, 42 mg (0.343 mmol) of phenyl boronic acid, 98 mg (0.515 mmol) of copper thiophencarboxylate and 20 mg (0.017 mmol) of palladium tetrakis were suspended in 1.5 mL of dry THF under argon atmosphere. The resulting suspension was heated a 130° C. for 1 h by microwave irradiation. The reaction mixture was then filtered on a silica plug, diluted with AcOEt and washed with aqueous NH4OH. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC/MS to provide the title compound (23%).

Workup

  1. filtrationThe reaction mixture was then filtered on a silica plug
  2. additiondiluted with AcOEt
  3. washwashed with aqueous NH4OH
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative HPLC/MS

Sources & evidence

ORD record
ord-9519fee0745e4a598eabea785ad7b1ed
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09284298B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes