Ammonium Sulfate → HCID 53997252, compound

HRID 1783510Notes

Reaction equation

HRID 1783510 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[NH:14][C:15]1[C:20]([C:21]#[N:22])=[CH:19][N:18]=[C:17]([S:23][CH3:24])[N:16]=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O1CCCC1>[NH2:22][CH2:21][C:20]1[C:15]([NH:14][CH:8]2[CH2:9][CH:10]3[CH2:13][CH:7]2[CH2:12][CH2:11]3)=[N:16][C:17]([S:23][CH3:24])=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 6097028Ammonium SulfateHCID 21226445Aluminium lithium hydrideHCID 53735900HCID 53735900, compound

Product 1

HCID 53997252HCID 53997252, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred 0° C. suspension of 2.5 g (65.3 mmol) of LAH in 100 mL of tetrahydrofuran is added dropwise a solution of 8.5 g (32.6 mmol) of 4-(bicyclo[2.2.1]hept-2-yl-amino)-2-(methylthio)-5-pyrimidinecarbonitrile in 375 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 four times with hot ethyl acetate. The combined organic washes are concentrated, and the residue is purified by chromatography on silica gel that is eluted with methanol/dichloromethane 1:9 followed by 2:8 to obtain 5.8 g (68%) of the title compound.

Workup

  1. customis recooled to 0° C.
  2. filtrationthe gray solids are filtered
  3. washwashed four times with hot ethyl acetate
  4. concentrationThe combined organic washes are concentrated
  5. customthe residue is purified by chromatography on silica gel that
  6. washis eluted with methanol/dichloromethane 1:9

Sources & evidence

ORD record
ord-179937a6095240cbb627441f080dc721
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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