Trimethyl borate → 8-Cyclopentyl-4-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-ylboronic acid

HRID 472203Notes

Reaction equation

HRID 472203 reaction equation
Br[C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7]([NH:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.C[O:22][B:23](OC)[O:24]C.[Li]CCCC>C1COCC1>[CH:16]1([N:13]2[C:5]3[N:6]=[C:7]([NH:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=3[CH:3]=[C:2]([B:23]([OH:24])[OH:22])[C:14]2=[O:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 592588576-Bromo-8-cyclopentyl-4-methyl-2-methylamino-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 178418339Butyllithium

Product 1

HCID 592588868-Cyclopentyl-4-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-ylboronic acidYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (−78° C.) solution of 6-bromo-8-cyclopentyl-4-methyl-2-(methylamino)-pyrido[2,3-d]pyrimidin-7(8H)-one (1.00 g, 2.94 mmol) and trimethylborate (1.40 mL, 12.6 mmol) in THF (60 mL) was added BuLi (9.5 mL, 1.6 M, 15.2 mmol). After stirring for 20 min, the mixture was quenched with small amount of 2 N HCl and water, extracted with EtOAc (3 times), dried and evaporated. The crude mixture was purified by silica gel chromatography to give the title compound (157.2 mg, 18%).

Workup

  1. stirringAfter stirring for 20 min
  2. customthe mixture was quenched with small amount of 2 N HCl and water
  3. extractionextracted with EtOAc (3 times)
  4. customdried
  5. customevaporated
  6. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b3dba03b311f42a5a0366b3211182d25
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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