Isopropylamine → 7-Chloro-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023301Notes

Reaction equation

HRID 1023301 reaction equation
Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:14])[N:3]=1.[CH:15]([NH2:18])([CH3:17])[CH3:16]>O1CCOCC1>[Cl:14][C:4]1[N:3]=[C:2]([NH:18][CH:15]([CH3:17])[CH3:16])[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 580929485,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

Product 1

HCID 580929447-Chloro-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-oneYield 86.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (920.2 mg, 4.0 mmol) and isopropylamine (1.7 mL, 1.182 g, 20.0 mmol) in dioxane (10 mL) was heated at 80° C. for 26 hours and evaporated to result in a residue which was partitioned between saturated NH4Cl solution (200 mL) and EtOAc (100 mL). The aqueous phase was extracted with EtOAc (2×50 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4, and evaporated to afford crude title product (872 mg, 86%). 1H NMR (DMSO-d6) δ 1.22 (d, J=6.4 Hz, 6H, 2CH3), 3.42 (s, 3H, NCH3), 4.19 (m, 1H), 6.59 (s, 1H), 8.45 (s, 1H), 8.90 (d, J=7.6 Hz, 1H, NH); ESI-MS m/z 253.1 (MH+).

Workup

  1. customevaporated
  2. customto result in a residue which
  3. customwas partitioned between saturated NH4Cl solution (200 mL) and EtOAc (100 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (2×50 mL)
  5. washthe combined organic phases were washed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-127ab75272ec41f386aa0647c98e788d
Source dataset
uspto-grants-2014_05
Patent number
US08722692B2

Reaction notes

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