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

HRID 2069147Notes

Reaction equation

HRID 2069147 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:27][O:28][CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[CH3:27][O:28][CH2:29][C:30]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[N:5]=[CH:4][N:3]=1)=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 229369424-Amino-6-(4-nitrophenoxy)pyrimidine

Product 1

HCID 708814382-Methoxy-N-(6-(4-nitrophenoxy)pyrimidin-4-yl)acetamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-6-(4-nitrophenoxy)pyrimidine (560 mg, 2.41 mmol) and DIPEA (630 μL, 3.62 mmol) in DCM (15 mL) under nitrogen at 0° C. was added 2-methoxyacetyl chloride (330 μL, 3.62 mmol) dropwise over 5 min. The mixture was warmed to RT for 1 hr and the reaction was quenched by addition of a 1% solution of NH3 in MeOH (10 mL) and then evaporated in vacuo. The residue was partitioned between DCM (50 mL) and water (25 mL) and the organic layer was separated and washed with brine (25 mL) and was then dried (MgSO4). Evaporation of the volatiles in vacuo gave the title compound as a beige solid (730 mg, 97%): Rt 1.87 min (Method 2); m/z 305 (M−H)+ (ES+).

Workup

  1. customthe reaction was quenched by addition of a 1% solution of NH3 in MeOH (10 mL)
  2. customevaporated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and water (25 mL)
  4. customthe organic layer was separated
  5. washwashed with brine (25 mL)
  6. dry with materialwas then dried (MgSO4)
  7. customEvaporation of the volatiles in vacuo

Sources & evidence

ORD record
ord-39bdcf01dcc147039697c86a763cf431
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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