Reaction #9825

Reaction equation

dimethylamine

tosylate

3-(2-bromo-phenyl)-3,4-dihydro-7-[2-(p-toluenesulfonyl)oxymethyl-benzodioxane-6-yl]amino-1-methyl-pyrimido[4,5-d]pyrimidin-2(1H)-one

→

3-(2-bromo-phenyl)-7-(2-dimethylaminomethyl-2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Solvents

NMP

THF

NMP

Conditions

Workup

1. 1
   TemperatureThe mixture was heated to 50° C. for 4 hrs
2. 2
   workup.WAITto 65° C. for another 2 hrs
3. 3
   workup.STIRRINGStirring
4. 4
   workup.WAITwas continued at 45° C. over night
5. 5
   OtherSeparation by HPLC-MS
6. 6
   Otheryielded crude product
7. 7
   Otherwas further purified
8. 8
   workup.DISSOLUTIONby dissolving in CHCl3
9. 9
   Washwashing with water

Procedure

90 mg of the tosylate from example 4 in 8 ml NMP were treated with 0.62 ml 2 M dimethylamine in THF and stirred at room temperature for 3 d. The mixture was heated to 50° C. for 4 hrs, then to 65° C. for another 2 hrs. Stirring was continued at 45° C. over night. Separation by HPLC-MS yielded crude product contaminated by NMP, which was further purified by dissolving in CHCl3 and washing with water.

Source