Hydroxyamine hydrochloride → HCID 178526381, compound

HRID 705574Notes

Reaction equation

HRID 705574 reaction equation
[F:1][C:2]1[C:3]([N:17]=[CH:18][N:19](C)C)=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.Cl.N[OH:24]>CCO>[F:1][C:2]1[C:3]([NH:17][CH:18]=[N:19][OH:24])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57818577HCID 57818577, compound

Product 1

HCID 178526381HCID 178526381, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N′-[5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]-N,N-dimethyl-formamidine (0.10 g, 0.34 mmol) in EtOH (2 mL) was added hydroxylamine hydrochloride (0.047 g, 0.68 mmol) and the mixture was agitated on an orbital shaker for 1.5 h at 50° C. The reaction mixture was cooled and evaporated to dryness. Water was added to produce a slurry which was filtered to isolate the title compound (0.090 g, 94% yield) as a white solid: mp 169-171° C.; 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=2.2 Hz, 1H), 8.02 (bs, 2H), 7.49-7.43 (m, 2H), 7.11-7.02 (m, 3H), 5.35 (s, 2H); HPLC-MS (ESI) m/z 281 (M+H)+, 279 (M−H)−.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. additionWater was added
  4. customto produce a slurry which
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-5cecc6e73e1c4edd99bc862a467c7209
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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