Hydrochloric Acid → HCID 86649361, compound

HRID 2401447Notes

Reaction equation

HRID 2401447 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12](C)[C:13](=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]=1.[ClH:21].O1CCOCC1>CO>[ClH:21].[ClH:21].[CH3:13][NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68786687HCID 68786687, compound

Product 1

HCID 86649361HCID 86649361, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of tert-butyl 3-(2-aminopyrimidin-4-ylamino)propyl(methyl)carbamate (Example 7A, 40 mg, 0.1422 mmol) in methanol (0.5 mL) was treated with a 4M solution of HCl in dioxane (0.5 mL, 2.0000 mmol). After stirring at ambient temperature for 18 hours, volatiles were removed under reduced pressure to give a white solid that was crystallized methanol/ether. White crystals were collected by filtration to provide N4-(3-(methylamino)propyl)pyrimidine-2,4-diamine dihydrochloride (6.0 mg, 16.6% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.01 (pentet, J=7 Hz, 2H), 2.72 (s, 3H), 3.07 (t, J=7 Hz, 2H), 3.58 (t, J=7 Hz, 2H), 6.13 (d, J=7 Hz, 1H), 7.58 (d, J=7 Hz, 1H). MS (DCl—NH3) m/z=182 (M+H)+.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customto give a white solid
  3. customthat was crystallized methanol/ether
  4. filtrationWhite crystals were collected by filtration

Sources & evidence

ORD record
ord-56f95a859439411bb9ef88b87af459ae
Source dataset
uspto-grants-2014_08
Patent number
US08796297B2

Reaction notes

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