Sodium hydride → HCID 67494327, compound

HRID 2047070Notes

Reaction equation

HRID 2047070 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[F:9])=[O:7].[CH3:18][Si:19]([CH3:50])([CH3:49])[CH2:20][CH2:21][O:22][CH2:23][N:24]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:25]1[N:30]2[N:31]=[CH:32][CH:33]=[C:29]2[N:28]=[C:27]([CH:34]2[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]2)[CH:26]=1>C1COCC1.C(Cl)Cl>[CH3:46][Si:45]([CH3:48])([CH3:47])[CH2:44][CH2:43][O:42][CH2:41][N:24]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:50])([CH3:49])[CH3:18])[C:25]1[N:30]2[N:31]=[CH:32][CH:33]=[C:29]2[N:28]=[C:27]([CH:34]2[CH2:39][CH2:38][C:37](=[C:8]([F:9])[C:6]([O:5][CH2:4][CH3:3])=[O:7])[CH2:36][CH2:35]2)[CH:26]=1

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 665836364-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone

Product 1

HCID 67494327HCID 67494327, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a 250 mL roundbottom flask containing 80 mL THF was charged sodium hydride (60% w/w in mineral oil, 12.86 mmol, 515 mg). This suspension was broken up in the sonicaid and then cooled to 0° C. in icebath. Triethyl 2-fluoro-2-phosphonoacetate (12.86 mmol, 3.12 g) was taken up in THF (10 mL) and added dropwise to stirring NaH suspension. The resulting solution was allowed to stir at 0° C. for 10 minutes. 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone (6.43 mmol, 3.16 g) was taken up in THF (10 mL) and added dropwise to the stirring solution. The reaction was allowed to warm to room temperature and stir 18 hours. At 18 hours, the reaction was diluted with DCM (400 mL) and washed with H2O. The organic layer was collected and dried over Na2SO4. This solution was reduced in vacuo and purified via flash chromatography to yield the title compound (3.43 g, 5.92 mmol).

Workup

  1. additionadded dropwise
  2. additionadded dropwise to the stirring solution
  3. temperatureto warm to room temperature
  4. stirringstir 18 hours
  5. waitAt 18 hours
  6. washwashed with H2O
  7. customThe organic layer was collected
  8. dry with materialdried over Na2SO4
  9. custompurified via flash chromatography

Sources & evidence

ORD record
ord-d6af6d281a9d481181338749a9054b91
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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