N-(2-Chlorophenyl)-6-morpholin-4-yl-5-nitro-2-(propylthio)pyrimidin-4-amine → N~4~-(2-Chlorophenyl)-6-morpholin-4-yl-2-(propylthio)pyrimidine-4,5-diamine

HRID 2116451Notes

Reaction equation

HRID 2116451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[C:13]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:12]=[C:11]([S:24][CH2:25][CH2:26][CH3:27])[N:10]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:14]([NH2:15])=[C:13]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[N:12]=[C:11]([S:24][CH2:25][CH2:26][CH3:27])[N:10]=1

Participants

4

Reactant 1

HCID 69215989N-(2-Chlorophenyl)-6-morpholin-4-yl-5-nitro-2-(propylthio)pyrimidin-4-amine

Product 1

HCID 131727106N~4~-(2-Chlorophenyl)-6-morpholin-4-yl-2-(propylthio)pyrimidine-4,5-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the product from step (ii) (0.82 g) and iron powder (1.2 g) in glacial acetic acid (40 ml) was stirred at room temperature until the starting material was consumed. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organics were dried (MgSO4) and evaporated under reduced pressure. Crude yield 0.82 g

Workup

  1. customwas consumed
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organics were dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5ac22856da434f9880765eca42773287
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

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