Methanol → 5,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[4,3-d]pyrimidin-4-amine

HRID 535358Notes

Reaction equation

HRID 535358 reaction equation
C(C1N[CH2:27][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]3[CH:26]=[CH:25][C:20]4[O:21][CH2:22][CH2:23][O:24][C:19]=4[CH:18]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+:32].[CH3:33]O>O.[Pd]>[O:21]1[CH2:22][CH2:23][O:24][C:19]2[CH:18]=[C:17]([NH:16][C:15]3[C:10]4[CH2:9][NH:32][CH2:33][CH2:27][C:11]=4[N:12]=[CH:13][N:14]=3)[CH:26]=[CH:25][C:20]1=2

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 684137456-benzyl-5,6,7,8-tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 593464955,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[4,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 6-benzyl-5,6,7,8-tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[3,4-d]pyrimidin-4-amine (0.742 g, 1.98 mmol), ammonium formate (1.25 g, 19.83 mmol) and palladium; 10% wt. on activated carbon (75 mg) in methanol (10 mL) is heated to 60° C. for 2 h. The mixture is cooled to r.t. and filtered over celite. The filtrate is concentrated under reduced pressure to give a white solid which is dissolved in water. The mixture is extracted twice with a 3:1 mixture of chloroform: isoproanol. The combined organic extracts are dried over sodium sulfate and concentrated to dryness to give the title compound.

Workup

  1. filtrationfiltered over celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customto give a white solid which
  4. extractionThe mixture is extracted twice with a 3:1 mixture of chloroform
  5. dry with materialThe combined organic extracts are dried over sodium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-256665615b3941398fb916d3a5abf7f1
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

Loading…