Sodium Hydroxide → HCID 22135460, compound

HRID 1826725Notes

Reaction equation

HRID 1826725 reaction equation
[OH-].[Na+].CC1(C)C(C)(C)OB([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)O1.[NH2:21][C:22]1[N:27]=[CH:26][C:25](Br)=[CH:24][N:23]=1>C1COCC1.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>[NH:15]1[C:16]2[C:12](=[C:11]([C:25]3[CH:24]=[N:23][C:22]([NH2:21])=[N:27][CH:26]=3)[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2313102-Amino-5-bromopyrimidineHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 22135460HCID 22135460, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pd(PPh3)4 (285 mg, 0.25 mmol) and a freshly prepared sodium hydroxide solution (985 mg in 12 mL of water) were added to a mixture of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole (2 g, 8.21 mmol) and 2-amino-5-bromopyrimidine (1.71 g, 9.85 mmol) in THF (30 mL). The reaction mixture was degassed and then purged three times with nitrogen and then refluxed overnight with stirring under nitrogen. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate (300 mL). The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give 1.4 g (82%) of 5-(1H-indol-4-yl)-pyrimidin-2-ylamine as a white solid.

Workup

  1. customThe reaction mixture was degassed
  2. custompurged three times with nitrogen
  3. temperaturerefluxed overnight
  4. additiondiluted with ethyl acetate (300 mL)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-409f909b11e64af09d010f5912c3e8f9
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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