Sodium borohydride → HCID 66803022, compound

HRID 341495Notes

Reaction equation

HRID 341495 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH2:15][CH2:16][O:17][CH3:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]2[N:23]=[C:22]([C:24]3[CH:25]=[CH:26][C:27]([C:30](OC)=[O:31])=[N:28][CH:29]=3)[O:21][N:20]=2)[N:3]=1.[BH4-].[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH2:15][CH2:16][O:17][CH3:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]2[N:23]=[C:22]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][OH:31])=[N:28][CH:29]=3)[O:21][N:20]=2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66802712HCID 66802712, compound

Product 1

HCID 66803022HCID 66803022, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(3-{4-amino-6-[(2-methoxyethyl)(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate (Example 311, 212 mg, 0.472 mmol) in anhydrous THF (50 mL) at 0 C, under nitrogen, was added sodium borohydride (45 mg, 1.18 mmol) portion-wise. The resulting reaction mixture was stirred at room temperature for 16 h and then quenched with a saturated ammonium chloride aq. solution (10 mL). The solution was extracted into EtOAc (3×25 mL) and combined organics washed with brine, dried over magnesium sulfate and evaporated to dryness to afford the title compound as a yellow solid (186 mg, 94%). Method C HPLC-MS: MH+ requires m/z=421. Found: m/z=421, Rt=1.19 min (73%).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with a saturated ammonium chloride aq. solution (10 mL)
  3. extractionThe solution was extracted into EtOAc (3×25 mL)
  4. washcombined organics washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a3e68607d1e74480a4023039f3f7afba
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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