Sodium hydride → HCID 59394726, compound

HRID 884634Notes

Reaction equation

HRID 884634 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[N:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH:27]1([C:30]2[N:34]([CH2:35][CH3:36])[N:33]=[C:32]([NH:37][C:38](=O)[O:39]C3C=CC=CC=3)[CH:31]=2)[CH2:29][CH2:28]1.[H-].[Na+]>C1COCC1>[CH:27]1([C:30]2[N:34]([CH2:35][CH3:36])[N:33]=[C:32]([NH:37][C:38]([N:1]3[C:9]4[C:4](=[CH:5][C:6]([O:10][C:11]5[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[N:12]=5)=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)=[O:39])[CH:31]=2)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59394365phenyl 5-cyclopropyl-1-ethyl-1H-pyrazol-3-ylcarbamateHCID 59394457tert-butyl (4-(1H-indol-5-yloxy)pyrimidin-2-yl)methyl(methyl)carbamate

Product 1

HCID 59394726HCID 59394726, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (4-(1H-indol-5-yloxy)pyrimidin-2-yl)methyl(methyl)carbamate (35 mg, 0.099 mmol) in THF (2 ml) is added phenyl 5-cyclopropyl-1-ethyl-1H-pyrazol-3-ylcarbamate (29.5 mg, 0.109 mmol), which is prepared as described in Example 5-S. The mixture is put at 0° C. and NaH (60% dispersion in oil; 11.85 mg, 0.296 mmol) is then added and the reaction is then stirred for 30 minutes. The reaction is then quenched with 10% AcOH/MeOH (0.3 mL) and further diluted with DCM and saturated aqueous NaHCO3. The resulting layers are then separated and the aqueous layer is extracted two additional times with DCM. The organic layers are combined, dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (10-100% EtOAc (2.5% EtOH)/DCM) to give the title compound. MS (ESI) m/z 532.3 (M+1).

Workup

  1. customis prepared
  2. customis put at 0° C.
  3. customThe reaction is then quenched with 10% AcOH/MeOH (0.3 mL)
  4. additionfurther diluted with DCM and saturated aqueous NaHCO3
  5. customThe resulting layers are then separated
  6. extractionthe aqueous layer is extracted two additional times with DCM
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue is purified via FCC (10-100% EtOAc (2.5% EtOH)/DCM)

Sources & evidence

ORD record
ord-4ed260a72c7846f79f7b46aee6476a7d
Source dataset
uspto-grants-2012_08
Patent number
US08242125B2

Reaction notes

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