Ammonium Chloride → 2-(3-Chlorophenyl)-5-pyrimidinamine

HRID 1626470Notes

Reaction equation

HRID 1626470 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 67287515HCID 67287515, compound

Product 1

HCID 431422892-(3-Chlorophenyl)-5-pyrimidinamineYield 28.8%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-(3-Chlorophenyl)-5-nitropyrimidine (100 mg, 0.424 mmol) was diluted with THF (1 mL) followed by the addition of Zn dust (27.8 mg, 0.424 mmol) and sat NH4Cl (1 mL). After stirring for 3 hours, the reaction was diluted with ethyl acetate and 10% sodium carbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a 0.5 mm preparative TLC plate eluting with 10% methanol/DCM to yield the desired compound (25 mg, 0.122 mmol, 28.6% yield).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified
  6. washeluting with 10% methanol/DCM

Sources & evidence

ORD record
ord-7093754e3a5c407fbeb6cd7df2a7350d
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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