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Ammonium Chloride → N-(4-Methoxybenzyl)-6-(4-amino-2-fluorophenoxy)pyrimidin-4-amine

HRID 2373949
Notes
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Reaction equation

HRID 2373949 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=3[F:25])[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[Cl-].[NH4+]>[Zn].CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=3[F:25])[N:12]=[CH:11][N:10]=2)=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 593016056-(2-Fluoro-4-nitrophenoxy)-N-(4-methoxybenzyl)pyrimidin-4-amine

Product 1

HCID 59301603N-(4-Methoxybenzyl)-6-(4-amino-2-fluorophenoxy)pyrimidin-4-amineYield 103.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 21899815MeOH tetrahydrofuran
Solvent

Procedure

A solution of N-(4-methoxybenzyl)-6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-amine (150 mg, 0.41 mmol) in 1:1 MeOH/THF (20 mL) was treated with ammonium chloride (0.22 g, 4.1 mmol), and zinc dust (<20 microns, 0.27 g, 4.2 mmol). The reaction mixture was stirred at RT for 1 h. An additional portion of zinc dust (150 mg) was added to the mixture and the reaction mixture was stirred at RT for 1 h and heated at 70° C. for 20 min. The mixture was filtered to remove the inorganic solids, concentrated in vacuo, and the residue partitioned between EtOAc and brine. The EtOAc phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (145 mg, 99%). 1H NMR (DMSO-d6) δ 8.10 (br s, 1H), 7.76 (br s, 1H), 7.21 (d, 2H, J=8.6 Hz), 6.88 (d, 3H, J=8.6 Hz), 6.44 (dd, 1H, J=12.7, 2.0 Hz), 6.36 (dd, 1H, J=8.3, 2.3 Hz), 5.79 (s, 1H), 4.41 (br s, 2H), 3.73 (s, 3H); MS(ESI+) m/z 341.18 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at RT for 1 h
  2. temperatureheated at 70° C. for 20 min
  3. filtrationThe mixture was filtered
  4. customto remove the inorganic solids
  5. concentrationconcentrated in vacuo
  6. customthe residue partitioned between EtOAc and brine
  7. customThe EtOAc phase was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a4a5a898b874f98894b9229f95d58b3
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07459562B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes