Ammonium Sulfate → HCID 54417160, compound

HRID 1783508Notes

Reaction equation

HRID 1783508 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([NH:12][C:13]2[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]([S:21][CH3:22])[N:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O1CCCC1>[NH2:20][CH2:19][C:18]1[C:13]([NH:12][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:14][C:15]([S:21][CH3:22])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 6097028Ammonium SulfateHCID 21226445Aluminium lithium hydrideHCID 38997210HCID 38997210, compound

Product 1

HCID 54417160HCID 54417160, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred 0° C. suspension of 1.7 g (44.8 mmol) of LAH in 70 mL of tetrahydrofuran is added dropwise a solution of 5.0 g (21.3 mmol) of 4-(cyclopentylamino)-2-(methylthio)-5-pyrimidinecarbonitrile in 250 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 chromatographed on silica gel eluting with 1:1:8 methanol/hexane/chloroform to obtain 4.0 g (79%) of the title compound: mp 58-60° C.

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 chromatographed on silica gel eluting with 1:1:8 methanol/hexane/chloroform

Sources & evidence

ORD record
ord-7ca619c1a25742b3a59e3bbf9e6f86c1
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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