Hydrochloric Acid → 2-(Methylamino)pyrimidine-4-carbaldehyde

HRID 969694Notes

Reaction equation

HRID 969694 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][CH3:11])[N:5]=1.Cl.C([O-])(O)=O.[Na+]>>[CH3:11][NH:10][C:6]1[N:5]=[C:4]([CH:3]=[O:2])[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178400144-(Dimethoxymethyl)-N-methylpyrimidin-2-amine

Product 1

HCID 220025312-(Methylamino)pyrimidine-4-carbaldehyde

Conditions

Temperature
48 °C

Procedure

(4-Dimethoxymethyl-pyrimidin-2-yl)-methylamine (Step A, 3.60 g, 19.6 mmol) and 3 N HCl (14.4 mL, 43.2 mmol) were combined and stirred at 48° C. for 17 h. After cooling to RT, 4.3 g of NaHCO3 was added in portions. The mixture was extracted with EtOAc, the combined organic portions were dried over MgSO4, filtered, and condensed to give the titled compound as a yellow solid. MS (ES+): 138.3 (M+H)+. Calc'd for C6H7N3O-137.14.

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined organic portions were dried over MgSO4
  4. filtrationfiltered
  5. customcondensed

Sources & evidence

ORD record
ord-5f22be3dba2c465781e64150dabb90f8
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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