Ammonium Chloride → HCID 9863005, compound

HRID 2252886Notes

Reaction equation

HRID 2252886 reaction equation
C1[O:18][CH2:17][CH2:16]OCCOCCOCCOCCOC1.COC(CP(=O)(OCC(F)(F)F)OCC(F)(F)F)=O.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:48][S:49][C:50]1[N:55]=[C:54]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:53]([CH:62]=O)=[C:52]([NH:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[N:51]=1.[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1.C(OCC)C>[CH3:48][S:49][C:50]1[N:55]=[C:54]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:53]2[CH:62]=[CH:16][C:17](=[O:18])[N:64]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[C:52]=2[N:51]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 184894Nsc 634137HCID 3251421Potassium bis(trimethylsilyl)amideHCID 9923140HCID 9923140, compound

Product 1

HCID 9863005HCID 9863005, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 18-crown-6 (422 mg, 1.6 mmol, 5 eq) and bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (81 μL, 0.38 mmol, 1.2 eq) in anhydrous THF (20 mL) was cooled to −78°. To this solution was added potassium bis(trimethylsilyl)amide (0.96 mL, 0.48 mmol, 1.5 eq) as a 0.5 mol solution in toluene. This solution was stirred for additional 30 min at −78° and 2-methylsulfanyl-4-phenyl-6-phenylamino-pyrimidine-5-carbaldehyde (102 mg, 0.32 mmol) in dry THF (1 mL) was added dropwise. The reaction mixture was then stirred for 8 h at −78° and warmed to 23° and stirred 16 h. Sat'd aq. NH4Cl (5 mL), followed by diethyl ether (20 mL), was added. The layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4), filtered and solvent was evaporated. The yellow residue was then purified by flash chromatography to afford 100 mg (91% yield) of pure 2-methylsulfanyl-4,8-diphenyl-8H-pyrido[2,3-d]pyrimidin-7-one. 1H-NMR δ 2.19 (s, 3H), 6.70 (d, 1H, J=9.9 Hz), 7.26 (m, 2H), 7.42-7.83 (m, 8H), 7.88 (d, 1H, J=9.9 Hz), LC MS (m/e)=346 (MH+).

Workup

  1. stirringThe reaction mixture was then stirred for 8 h at −78°
  2. temperaturewarmed to 23°
  3. stirringstirred 16 h
  4. additionwas added
  5. customThe layers were separated
  6. washThe organic layer was washed with satd aq NaCl
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customsolvent was evaporated
  10. customThe yellow residue was then purified by flash chromatography

Sources & evidence

ORD record
ord-ce696537d8184f0f936317693185b57b
Source dataset
uspto-grants-2008_01
Patent number
US07323472B2

Reaction notes

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