Acetonitrile → HCID 18507610, compound

HRID 1356186Notes

Reaction equation

HRID 1356186 reaction equation
[C:1](#[N:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:14][C:15]1[N:20]=[C:19]([C:21]2[O:22][C:23](Br)=[CH:24][CH:25]=2)[C:18]([C:27]#[N:28])=[C:17]([S:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[N:16]=1>C1COCC1>[NH2:14][C:15]1[N:20]=[C:19]([C:21]2[O:22][C:23]([CH2:2][C:1]#[N:3])=[CH:24][CH:25]=2)[C:18]([C:27]#[N:28])=[C:17]([S:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[N:16]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 18507483HCID 18507483, compound

Product 1

HCID 18507610HCID 18507610, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 0.2 ml (3.72 mmol) acetonitrile in 25 ml dry THF under argon at −78° C. was added dropwise 3.3 ml (1,65 mmol) potassium bis(trimethylsilyl)amide solution (0.5M in toluene) and stirring continued for 1 hour. The solution was then transferred dropwise via cannula to a solution of 300 mg (0.75 mmol) 2-amino-4-(5-bromo-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile in 25 ml THF at −78° C. and stirring continued for 5 h at −78° C. and 1 h at −40° C. The reaction mixture was then quenched by addition of saturated aqueous ammonium chloride solution. The mixtured was extracted twice with ethyl acetate and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 4/1 then ethyl acetate) afforded 22 mg (8%) 2-amino-4-(5-cyanomethyl-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile as a brown crystalline solid. ES-MS m/e (%): 385 (M+Na+, 45), 363 (M+H+, 100).

Workup

  1. stirringstirring
  2. waitcontinued for 5 h at −78° C. and 1 h at −40° C
  3. customThe reaction mixture was then quenched by addition of saturated aqueous ammonium chloride solution
  4. extractionThe mixtured was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e8866c808364dfa90bd3b23e185e96e
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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