Lithium Hexamethyldisilazide → 5-amino-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2386662Notes

Reaction equation

HRID 2386662 reaction equation
[C:1]([C:3]1[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[NH2:2][C:1]1[C:3]2[CH:8]=[N:7][C:6]([S:9][CH3:10])=[N:5][C:4]=2[N:11]([CH3:15])[C:12](=[O:14])[CH:13]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 57929481N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-methyl-acetamide

Product 1

HCID 579294685-amino-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-methyl-acetamide (400 mg, 1.80 mmol) in THF (18 mL) was added a solution of lithium bis(trimethyl-silyl)amide (1.0 M in hexane, 7.2 mL, 7.20 mmol) at RT. The reaction mixture was stirred at RT for 1 h, then quenched with water (100 mL). The resulting mixture was extracted with EtOAc (100 mL); the organic layer dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography (from 10 to >100% EtOAc/hexane in 10 min.) to give 163 mg (41% yield) of 5-amino-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]-pyrimidin-7-one as a yellow solid.

Workup

  1. customquenched with water (100 mL)
  2. extractionThe resulting mixture was extracted with EtOAc (100 mL)
  3. dry with materialthe organic layer dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (from 10 to >100% EtOAc/hexane in 10 min.)

Sources & evidence

ORD record
ord-877c7489c9754e57bb8f5b12d38b7770
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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