Water → 1-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethan-1-ol

HRID 341500Notes

Reaction equation

HRID 341500 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[N:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=3)[O:18][N:17]=2)[N:3]=1.[BH4-].[Na+].CCOC(C)=O.O>C1COCC1>[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[N:26]=[CH:25][C:24]([CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=3)[O:18][N:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 668026271-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-3-yl]ethan-1-one2×

Product 1

HCID 668031951-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethan-1-olYield 106.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-3-yl]ethan-1-one (Intermediate 141, 0.934 g, 2.40 mmol) was suspended in THF (60 mL), sodium borohydride (0.227 g, 6.01 mmol) was added and the mixture stirred at room temperature for 2 h. EtOAc (50 mL) and water (100 mL) were added and the organic layer separated. The aqueous layer was neutralised using 1M aq. hydrochloric acid and extracted with EtOAc (3×30 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford the title compound as a pale yellow solid (1.0 g), which was used in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=391 Found: m/z=391, Rt=1.18 min (84%).

Workup

  1. customthe organic layer separated
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e1c13c80164a46d58265cc21823a951c
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…