Sodium t-butoxide → HCID 23653612, compound

HRID 1365884Notes

Reaction equation

HRID 1365884 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([C:20]#[C:21][C:22]4[CH:23]=[N:24][C:25]([NH2:28])=[N:26][CH:27]=4)[C:14]3=[O:29])[CH:11]=2)[C:6]([CH3:31])([CH3:30])[CH2:5]1)(=O)C.CC(C)([O-])C.[Na+]>CC(O)(C)C.CCOC(C)=O>[NH2:28][C:25]1[N:24]=[CH:23][C:22]([C:21]#[C:20][C:15]2[C:14](=[O:29])[N:13]([C:10]3[CH:11]=[C:12]4[C:7]([C:6]([CH3:31])([CH3:30])[CH2:5][NH:4]4)=[CH:8][CH:9]=3)[CH:18]=[CH:17][C:16]=2[CH3:19])=[CH:27][N:26]=1

Participants

5

Reactant 2

HCID 23676156Sodium t-butoxideHCID 25055365HCID 25055365, compound

Product 1

HCID 23653612HCID 23653612, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-3-((2-amino-5-pyrimidinyl)ethynyl)-4-methyl-2(1H)-pyridinone (0.103 g, 0.25 mmol) and sodium tert-butoxide (0.072 g, 0.75 mmol) in tBuOH (4 mL) was heated under microwave radiation at 100° C. for 10 min. The reaction mixture was diluted with EtOAc and washed with saturated NH4Cl and brine. The solids formed were filtered and recombined with the organic fraction. After concentrating the organic fraction in vacuo, the residue was purified by silica gel chromatography using 0-10% MeOH in EtOAc to afford 3-((2-amino-5-pyrimidinyl)ethynyl)-1-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-4-methyl-2(1H)-pyridinone as a light yellow solid. Found M+H+=372.3.

Workup

  1. washwashed with saturated NH4Cl and brine
  2. customThe solids formed
  3. filtrationwere filtered
  4. concentrationAfter concentrating the organic fraction in vacuo
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3debb9b6f3c74c44a8e3523aeef711fb
Source dataset
uspto-grants-2011_02
Patent number
US07893061B2

Reaction notes

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