Dimethylamine → 908269-95-4

HRID 1446702Notes

Reaction equation

HRID 1446702 reaction equation
[Li+].C[CH:3]([N-:5][CH:6](C)C)C.CNC.C[O:13][C:14]([C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=1)=O>>[NH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][N:19]=1)[C:14]([N:5]([CH3:6])[CH3:3])=[O:13]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 62154659908269-95-4

Conditions

Temperature
85 °C

Procedure

To LDA (7.3 mL, 13 mmol, 1.8M in ether/heptane) at 0° C., add dropwise dimethylamine (13 mL, 26 mmol, 2M in THF) under nitrogen. Stir for 30 minutes and add 2-amino-4-pyridine carboxylic acid methyl ester (2 g, 13 mmol, in 3 mL of anhydrous THF and 2 mL of anhydrous ether). Seal and heat at 85° C. overnight. Cool the mixture to room temperature and quench with water. Dilute with EtOAc and isolate the top organic layer. Extract the aqueous layer further with saturated sodium bicarbonate and ether, then DCM. Pool all the organic layers, dry (MgSO4) and concentrate. Purify by strong cation exchange (SCX) column to obtain the crude product and use in the next step without further purification. LCMS (ES), m/z 166 (M+1).

Workup

  1. customSeal
  2. temperatureCool the mixture to room temperature
  3. customquench with water
  4. additionDilute with EtOAc
  5. customisolate the top organic layer
  6. extractionExtract the aqueous layer further with saturated sodium bicarbonate and ether
  7. dry with materialPool all the organic layers, dry (MgSO4)
  8. concentrationconcentrate
  9. customPurify by strong cation exchange (SCX) column

Sources & evidence

ORD record
ord-162ab913f343489eadaed34439dda914
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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