Ammonium formate → HCID 117870770, compound

HRID 530620Notes

Reaction equation

HRID 530620 reaction equation
[CH:1]([C:4]1[N:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].[CH:12]([O-])=O.[NH4+:15]>[N+](C)([O-])=O>[NH2:15][CH2:12][CH:10]([C:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:9]=1)[OH:11]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 280651282-(Propan-2-yl)pyrimidine-4-carbaldehyde

Product 1

HCID 117870770HCID 117870770, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a 100 mL round-bottomed flask, 2-isopropylpyrimidine-4-carbaldehyde (865 mg, 5.76 mmol) was combined with nitromethane (7.00 ml) to give a colorless solution. TEA (583 mg, 803 μl, 5.76 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. Complete by LCMS. The reaction mixture was concentrated in vacuo, kept on the vacuum pump for 30 min. and used as is immediately. The resulting yellow oil was taken up in 20 mL of THF and 20 mL of methanol and placed under a nitrogen atmosphere. To that was added 240 mg of 10% Pd/C (pre-wet with ethanol). Ammonium formate (1.82 g, 28.8 mmol) was added. The reaction mixture was stirred at room temperature for 2 days. Complete by LCMS. The reaction mixture was purged with argon, filtered through Celite and the filtercake washed several times with methanol. The combined filtrate and washes were concentrated in vacuo and loaded onto column in dichloromethane/methanol approx. 95:5. The crude material was purified by flash chromatography (silica gel, 40 g, 10% to 50% [(60:10:1 dichloromethane:MeOH:NH4OH) in dichloromethane gradient] to afford 2-amino-1-(2-isopropylpyrimidin-4-yl)ethanol (0.54 g) as a white solid. (M+H)+=182 m/e.

Workup

  1. customto give a colorless solution
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. waitkept on the vacuum pump for 30 min.
  4. additionTo that was added 240 mg of 10% Pd/C (pre-wet with ethanol)
  5. stirringThe reaction mixture was stirred at room temperature for 2 days
  6. customThe reaction mixture was purged with argon
  7. filtrationfiltered through Celite
  8. washthe filtercake washed several times with methanol
  9. concentrationThe combined filtrate and washes were concentrated in vacuo
  10. customThe crude material was purified by flash chromatography (silica gel, 40 g, 10% to 50% [(60:10:1 dichloromethane:MeOH:NH4OH) in dichloromethane gradient]

Sources & evidence

ORD record
ord-e7cc2fd930044614bcfcf2e60916612e
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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