Sodium Carbonate → 5-(2-Aminopyrimidin-5-yl)picolinic acid

HRID 500178Notes

Reaction equation

HRID 500178 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)O1.C[O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][N:28]=1)=[O:26]>O.C(O)C.C1(C)C=CC=CC=1.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>[NH2:21][C:18]1[N:19]=[CH:20][C:15]([C:30]2[CH:31]=[CH:32][C:27]([C:25]([OH:26])=[O:24])=[N:28][CH:29]=2)=[CH:16][N:17]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

Product 1

HCID 672237795-(2-Aminopyrimidin-5-yl)picolinic acidYield 58%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.442 g, 2.0 mmol), 5-bromopyridine-2-carboxylic acid methyl ester (0.518 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in ethanol (3.0 mL) and toluene (3.0 mL). The resulting mixture was heated at 120° C. for 3 h. The organic solvents were removed under reduced pressure. The residue was diluted with water, and adjusted with 1N HCl to pH=4. The precipitates were collected by filtration, washed with water and EtOAc, and dried to give the desired product (0.25 g, 58%). LCMS: (M+H)=217.0.

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water and EtOAc
  5. customdried

Sources & evidence

ORD record
ord-3ed1e76a009e4a60ad1ea18cc7432f40
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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