Hydrochloric Acid → HCID 68294548, compound

HRID 2279494Notes

Reaction equation

HRID 2279494 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=[N:3]1.Cl.O1CCOCC1.N.CO>C(Cl)Cl.CCO>[CH3:1][N:2]1[C:6]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][NH:15][CH2:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 21705897Ammonia methanolHCID 68294481HCID 68294481, compound

Product 1

HCID 68294548HCID 68294548, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of tert-butyl 2-(1-methyl-1H-pyrazol-5-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.556 g, 1.68 mmol) in DCM/EtOH 5 mL, 1:1) was added 4N HCl in dioxane (4.21 ml, 16.8 mmol) and the solution stirred for 18 h. The reaction was concentrated to afford an orange solid that was neutralized by stirring with 7N NH3/MeOH and washed with DCM. The precipitate was filtered and purified by SiO2 chromatography (SNAP 25) eluting with a MeOH/DCM gradient (0 to 20% MeOH) to afford 0.223 g (75% purity, 44% yield) of N-(1-methyl-1H-pyrazol-5-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine (184) as a light yellow solid: MS m/z (APCI-pos) M+1=231.2.

Workup

  1. concentrationThe reaction was concentrated
  2. customto afford an orange solid
  3. washwashed with DCM
  4. filtrationThe precipitate was filtered
  5. custompurified by SiO2 chromatography (SNAP 25)
  6. washeluting with a MeOH/DCM gradient (0 to 20% MeOH)

Sources & evidence

ORD record
ord-61486b27b7a44df5bda7e67381684219
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…