Hydrochloric Acid → HCID 58138258, compound

HRID 1967565Notes

Reaction equation

HRID 1967565 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH:13]C(=O)C)([CH3:12])[CH3:11])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH2:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66911094HCID 66911094, compound

Product 1

HCID 58138258HCID 58138258, compoundYield 36%

Procedure

Heat a solution of N-[1-(2-cyclopropyl-pyrimidin-4-yl)-1-methyl-ethyl]-acetamide (4.5 g, 20.5 mmol) and aqueous 5N HCl (125 mL) to 100° C. for 18 hours. Cool the mixture to room temperature. Extract the reaction with diethyl ether (2×) then make the aqueous layer alkaline with aqueous 5N NaOH. Extract the aqueous layer with diethyl ether (3×), dry the combined organic layers over sodium sulfate, filter, and concentrate under reduced pressure to give 1-(2-cyclopropyl-pyrimidin-4-yl)-1-methyl-ethylamine (1.3 g, 36%) as a dark yellow oil. 1H NMR (400 MHz, CDCl3): δ 8.45 (d, J=5.6 Hz, 1H), 7.12 (d, J=5.6 Hz, 1H), 2.30 (m, 1H), 1.76 (br s, 2H), 1.41 (s, 6H), 1.09 (m, 2H), 1.02 (m, 2H).

Workup

  1. extractionExtract
  2. customthe reaction with diethyl ether (2×)
  3. extractionExtract the aqueous layer with diethyl ether (3×)
  4. dry with materialdry the combined organic layers over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-62e85c6d840547adb6558293659ee25d
Source dataset
uspto-grants-2013_04
Patent number
US08420654B2

Reaction notes

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