Ammonium Chloride → HCID 86629446, compound

HRID 599289Notes

Reaction equation

HRID 599289 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][N:7]([C:12]3[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([F:21])=[CH:14][C:13]=3[CH3:22])[C:6](=[O:23])[N:5]([CH3:24])[C:4]=2[CH:3]=1.[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[NH2:18][C:16]1[C:15]([F:21])=[CH:14][C:13]([CH3:22])=[C:12]([N:7]2[CH2:8][C:9]3[CH:10]=[N:11][C:2]([Cl:1])=[CH:3][C:4]=3[N:5]([CH3:24])[C:6]2=[O:23])[CH:17]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86629444HCID 86629444, compound

Product 1

HCID 86629446HCID 86629446, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Zn Dust (0.575 g, 8.80 mmol) was added to a suspension of 7-chloro-3-(4-fluoro-2-methyl-5-nitrophenyl)-1-methyl-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (0.309 g, 0.880 mmol) and NH4Cl (0.471 g, 8.80 mmol in MeOH/THF (1:1, 16 mL) and the mixture was stirred 1.5 h at RT. The mixture was filtered through Celite, rinsing forward with MeOH and the filtrates were concentrated, diluted with brine and extracted with THF (2×). The combined organics layers were washed with brine, dried (MgSO4), and concentrated to afford 3-(5-amino-4-fluoro-2-methylphenyl)-7-chloro-1-methyl-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (0.260 g, 92% yield). MS (ESI) m/z: 321.0 [M+H+].

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washrinsing forward with MeOH
  3. concentrationthe filtrates were concentrated
  4. additiondiluted with brine
  5. extractionextracted with THF (2×)
  6. washThe combined organics layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3ae986be0ade495eb0d2fb2c221f71b9
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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