2-Amino-6-methoxypyrimidine-4-carbonitrile → 4-(Aminomethyl)-6-methoxypyrimidin-2-amine

HRID 2071018Notes

Reaction equation

HRID 2071018 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1>CC(O)=O.[Pd]>[NH2:9][CH2:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

4

Reactant 1

HCID 141292502-Amino-6-methoxypyrimidine-4-carbonitrile

Product 1

HCID 595697334-(Aminomethyl)-6-methoxypyrimidin-2-amineYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% Pd/C (0.010 g) was added to a stirred solution of 2-amino-6-methoxypyrimidine-4-carbonitrile (0.107 g, 0.71 mmol, 1 eq) in 4 ml HOAc. A H2 balloon (20 psi) was added. After 2 h the mixture was filtered through Celite. The filter cake was rinsed with MeOH. The organics were combined and the solvent was removed in vacuo. 1 N NaOH was added to pH>8 and the solvent was removed in vacuo. The residue was stirred in EtOAc (30 ml) and saturated aqueous NaHCO3 (1 ml). After 30 min Na2SO4 was added and the mixture was stirred for 10 min. The inorganics were filtered off, and the solvent was removed in vacuo yielding 0.1044 g (0.68 mmol, 95% yield) of the product.

Workup

  1. additionA H2 balloon (20 psi) was added
  2. filtrationAfter 2 h the mixture was filtered through Celite
  3. washThe filter cake was rinsed with MeOH
  4. customthe solvent was removed in vacuo
  5. addition1 N NaOH was added to pH>8
  6. customthe solvent was removed in vacuo
  7. additionAfter 30 min Na2SO4 was added
  8. stirringthe mixture was stirred for 10 min
  9. filtrationThe inorganics were filtered off
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5177e188d82247d49caf5378988ba78b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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