Sodium borohydride → [5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-2-yl}methanol

HRID 341435Notes

Reaction equation

HRID 341435 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27](OC)=[O:28])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1.[BH4-].[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][OH:28])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66803428Methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate

Product 1

HCID 66802820[5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-2-yl}methanolYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate (prepared in an analogous manner to Example 279, 500 mg, 1.23 mmol) in anhydrous THF (50 mL) at 0 C, was added sodium borohydride (95 mg, 2.46 mmol) portion-wise under nitrogen. The resulting solution was sonicated briefly and stirred at 40 C for 1 h. The reaction mixture was then allowed to stir at room temperature for a further 16 h. The reaction was quenched with water (25 mL) and extracted with EtOAc (3×25 mL). Combined organics were dried over magnesium sulfate and evaporated to dryness to afford the crude product as a yellow solid. The solid was triturated with MeOH, filtered and washed further with diethyl ether (100 mL) to afford the title compound as a salmon coloured solid (305 mg, 67%).

Workup

  1. customThe resulting solution was sonicated briefly
  2. stirringto stir at room temperature for a further 16 h
  3. customThe reaction was quenched with water (25 mL)
  4. extractionextracted with EtOAc (3×25 mL)
  5. dry with materialCombined organics were dried over magnesium sulfate
  6. customevaporated to dryness
  7. customto afford the crude product as a yellow solid
  8. customThe solid was triturated with MeOH
  9. filtrationfiltered
  10. washwashed further with diethyl ether (100 mL)

Sources & evidence

ORD record
ord-8f11c3c466934f5e8a8631b7d92ee6fb
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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