N,O-Dimethylhydroxylamine → 6-Chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide

HRID 469300Notes

Reaction equation

HRID 469300 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([C:17](Cl)=[O:18])[CH:12]=1.[CH3:20][NH:21][O:22][CH3:23]>C(Cl)Cl>[CH3:23][O:22][N:21]([CH3:20])[C:17]([C:13]1[CH:12]=[C:11]([Cl:10])[N:16]=[CH:15][N:14]=1)=[O:18]

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 581812166-Chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

20.7 mL (0.120 mol) DIPEA were added at 0° C. to 10.7 g (54.4 mmol) 6-chloropyrimidine-4-carboxylic acid chloride and 5.50 g (56.4 mmol) N,O-dimethylhydroxylamine in 150 mL DCM and stirred for 1 h at 0° C. and 1 h at RT. The mixture was diluted with DCM and washed with water. The organic phase was dried on sodium sulphate, filtered and evaporated down.

Workup

  1. washwashed with water
  2. customThe organic phase was dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down

Sources & evidence

ORD record
ord-8b437771f8824af9836eb3de4a1f57ee
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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