2-Methoxy-N-(6-(4-nitrophenoxy)pyrimidin-4-yl)acetamide → N-(6-(4-Aminophenoxy)pyrimidin-4-yl)-2-methoxyacetamide

HRID 2069148Notes

Reaction equation

HRID 2069148 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[N:10]=[CH:9][N:8]=1)=[O:5].[H][H]>CO.C(Cl)Cl.CC(O)=O.[Pt]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:11]2[N:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 2

HCID 708814382-Methoxy-N-(6-(4-nitrophenoxy)pyrimidin-4-yl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 86660489N-(6-(4-Aminophenoxy)pyrimidin-4-yl)-2-methoxyacetamide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxy-N-(6-(4-nitrophenoxy)pyrimidin-4-yl)acetamide (730 mg, 2.53 mmol) in a mixture of MeOH and DCM (1:1 v/v, 80 mL) containing AcOH (5 drops) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 10% Pt/C, full hydrogen mode) and was then evaporated in vacuo. The residue was partitioned between DCM (100 mL) and saturated aq NaHCO3 solution (25 mL). The organic layer was separated and washed with brine (25 mL) and then dried (MgSO4). Evaporation of the volatiles in vacuo gave the title compound, Intermediate N1, (560 mg, 66%, estimated 82% purity); Rt 0.93 min (Method 2); m/z 275 (M+H)+ (ES+). This material was used directly in the next step without further purification.

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was partitioned between DCM (100 mL) and saturated aq NaHCO3 solution (25 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the volatiles in vacuo

Sources & evidence

ORD record
ord-66f1fa99818c40ec93880a91efcc583e
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

Loading…