Hydroxyamine hydrochloride → HCID 178513438, compound

HRID 1500057Notes

Reaction equation

HRID 1500057 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]#[N:17])[C:12]([F:18])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21]>C(O)CCC>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([NH:20][OH:21])=[NH:17])[C:12]([F:18])=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 59160647HCID 59160647, compound

Product 1

HCID 178513438HCID 178513438, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-benzyloxy-5-fluoro-pyrimidin-4-yl-cyanamide (2.9 g, 0.012 mol) in n-butanol (30 mL) in a 100 mL sealed tube was added hydroxylamine hydrochloride (4.1 g, 0.059 mol) and the solution was heated at 110° C. for 2 h. The reaction was cooled and checked by TLC and was determined to be complete. The solvent was removed in vacuo and the resulting mixture was diluted with water and extracted with EtOAc (3×30 mL). The organic layers were dried over Na2SO4, filtered, and evaporated. The crude product was purified further with reverse phase chromatography to yield the title compound (500 mg, 15% yield) as an off white solid; mp 150-152 dec.; 1H NMR (300 MHz, DMSO-d6) δ 8.72 (s, 2H), 8.44 (d, J=2.6 Hz, 1H), 7.41 (m, J=13.8, 6.3 Hz, 5H), 5.34 (s, 2H); MS (EI) m/z 278 (M)+.

Workup

  1. temperatureThe reaction was cooled
  2. customThe solvent was removed in vacuo
  3. additionthe resulting mixture was diluted with water
  4. extractionextracted with EtOAc (3×30 mL)
  5. dry with materialThe organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified further with reverse phase chromatography

Sources & evidence

ORD record
ord-046406b549a641a19b65996d4772f13a
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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