Sodium sulfide nonahydrate → HCID 86717499, compound

HRID 712044Notes

Reaction equation

HRID 712044 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:6]2[CH:5]=[N:4][C:3]=1[C:12]#[C:13][Si](C)(C)C.O.O.O.O.O.O.O.O.O.[S-2:27].[Na+].[Na+]>CN(C)C=O>[CH3:11][C:9]1[N:10]=[C:6]2[CH:5]=[N:4][C:3]3[CH:12]=[CH:13][S:27][C:2]=3[N:7]2[CH:8]=1

Participants

4

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 86717497HCID 86717497, compound

Product 1

HCID 86717499HCID 86717499, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-methyl-6-[(trimethylsilyl)ethynyl]imidazo[1,2-a]pyrazine (0.400 g, 1.52 mmol), and sodium sulfide nonahydrate (1.09 g, 4.55 mmol) in N,N-dimethylformamide (6.0 mL) was heated in a preheated oil bath at 100° C. with stirring for 1 h. The reaction was cooled and partitioned between EtOAc and water. The organic layer was washed with water, brine, dried and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with EtOAc and 3% MeOH in EtOAc to give the desired product (0.15 g, 52%). LCMS calculated for C9H8N3S (M+H)+: m/z=190.0. Found: 190.0.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica gel eluting with EtOAc and 3% MeOH in EtOAc

Sources & evidence

ORD record
ord-65b9165181964ef6a146cc840c92bda7
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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