Ammonium formate → N-(4-tert-butylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971191Notes

Reaction equation

HRID 971191 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH2:21][CH2:20][N:19](CC4C=CC=CC=4)[CH2:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.O.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH2:21][CH2:20][NH:19][CH2:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 11383178HCID 11383178, compound

Product 1

HCID 59021490N-(4-tert-butylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amineYield 95.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(4-tert-butylphenyl)-7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (0.359 g, 0.96 mmol), prepared as described in Example 2, ammonium formate (0.304 g, 4.82 mmol) and palladium (10% wt. on activated carbon, 40 mg) in MeOH (5 mL) was stirred at r.t. for 1 h and then at 60° C. for 2 h. The mixture was cooled to r.t. and filtered over celite. The filtrate was concentrated under reduced pressure to give a white solid which was dissolved in water. The mixture was extracted twice with a 3:1 mixture of chloroform:isopropanol. The combined organic extracts were dried over sodium sulfate and concentrated to dryness to give 0.26 g of the title compound which was used directly without further purification.

Workup

  1. customprepared
  2. waitat 60° C. for 2 h
  3. temperatureThe mixture was cooled to r.t.
  4. filtrationfiltered over celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a white solid which
  7. extractionThe mixture was extracted twice with a 3:1 mixture of chloroform
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-abf765e992c3493684551176079a3a3b
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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