Triphenylphosphine → (5-Aminomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine 2HCl

HRID 2216279Notes

Reaction equation

HRID 2216279 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([NH:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:7][C:8]([Cl:11])=[N:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[ClH:11].[ClH:11].[NH2:1][CH2:4][C:5]1[C:6]([NH:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:7][C:8]([Cl:11])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 21941878(5-Azidomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine

Product 1

HCID 21941877(5-Aminomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine 2HCl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.47 g (15.77 mmol) (5-azidomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine and 1.67 g (6.35 mmol) of triphenylphosphine in 20 ml of THF and 0.08 ml of H2O is stirred at r.t. for 24 h. Then the solvent is removed and the residue dissolved in 40 ml EtOH and 17 ml NH3 (25%). This reaction mixture is stirred for 48 h at r.t. and again the solvent is removed. The residue is dissolved in diethylether and twice extracted with 25 ml of 1N HCl. Both acidic extracts were combined and once more extracted with diethylether, then the acidic layer is evaporated under vacuo. The solid residue was triturated with diethylether yielding (5-Aminomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine 2HCl as slightly yellow crystalls.

Workup

  1. customThen the solvent is removed
  2. dissolutionthe residue dissolved in 40 ml EtOH
  3. customagain the solvent is removed
  4. dissolutionThe residue is dissolved in diethylether
  5. extractiontwice extracted with 25 ml of 1N HCl
  6. extractiononce more extracted with diethylether
  7. customthe acidic layer is evaporated under vacuo
  8. customThe solid residue was triturated with diethylether

Sources & evidence

ORD record
ord-1318c320f7ff447593a598f453c6e2e1
Source dataset
uspto-grants-2006_09
Patent number
US07112589B2

Reaction notes

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