Ammonium Sulfate → 5-(Aminomethyl)-4-(isopropylamino)-2-(methylthio)pyrimidine

HRID 1783509Notes

Reaction equation

HRID 1783509 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([NH:10][C:11]1[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=1)([CH3:9])[CH3:8].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O1CCCC1>[NH2:18][CH2:17][C:16]1[C:11]([NH:10][CH:7]([CH3:9])[CH3:8])=[N:12][C:13]([S:19][CH3:20])=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 6097028Ammonium SulfateHCID 21226445Aluminium lithium hydrideHCID 538348074-[(1-Methylethyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile

Product 1

HCID 541509035-(Aminomethyl)-4-(isopropylamino)-2-(methylthio)pyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred 0° C. suspension of 5.9 g (156.3 mmol) of LAH in 200 mL of tetrahydrofuran is added dropwise a solution of 15.5 g (74.4 mmol) of 4-(isopropylamino)-2-(methylthio)-5-pyrimidinecarbonitrile in 500 mL of tetrahydrofuran. The reaction is allowed to warm slowly to room temperature overnight. The mixture is recooled to 0° C., and treated with a saturated solution of ammonium sulfate until there is no more effervescence. After stirring for another 15 minutes, the gray solids are filtered and washed six times with hot ethyl acetate. The combined organic washes are concentrated, and the residue is purified by chromatography in two portions on a 4×15 cm Biotage silica gel column that is eluted with 60:38:2 acetonitrile/dichloromethane/triethylamine followed by 60:33:5:2 acetonitrile/dichloromethane/methanol/triethylamine to obtain 12.9 g (82%) of the title compound as a yellow oil. Mass Spectrum (CI) (m+1)/z 213.

Workup

  1. customis recooled to 0° C.
  2. filtrationthe gray solids are filtered
  3. washwashed six times with hot ethyl acetate
  4. concentrationThe combined organic washes are concentrated
  5. customthe residue is purified by chromatography in two portions on a 4×15 cm Biotage silica gel column that
  6. washis eluted with 60:38:2 acetonitrile/dichloromethane/triethylamine

Sources & evidence

ORD record
ord-3d28e01008034d64a935c8ec65db738f
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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