Hydrochloric Acid → HCID 86696649, compound

HRID 1774148Notes

Reaction equation

HRID 1774148 reaction equation
Cl.F[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:10]=2)[CH:6]=[CH:5][N:4]=1.C([O-])(O)=[O:23].[Na+]>>[O:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:11]2[N:10]=[C:9]([C:7]3[CH:6]=[CH:5][NH:4][C:3](=[O:23])[CH:8]=3)[CH:14]=[CH:13][N:12]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86696650HCID 86696650, compound

Product 1

HCID 86696649HCID 86696649, compoundYield 94%

Procedure

1M HCl (35 mL) was added to 4-(2-fluoropyridin-4-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-amine (0.32 g, 1.2 mmol). The mixture was heated at reflux overnight. The cooled reaction mixture was neutralized with solid NaHCO3. The resulting solid was collected by vacuum filtration, washed into a flask with EtOAc/MeOH, evaporated and dried to afford 4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.30 g, 1.1 mmol, 94% yield). 1H NMR (400 MHz, (CD3)2SO) δ 11.74 (br s, 1H), 8.40 (d, 1H), 7.48 (d, 1H), 7.33 (d, 1H), 7.11 (d, 1H), 6.99 (br s, 1H), 6.85-6.76 (m, 1H), 4.04-3.92 (m, 1H), 3.92-3.85 (m, 2H), 3.45-3.36 (m, 2H), 1.90-1.81 (m, 2H), 1.59-1.48 (m, 2H); m/z (APCI-pos) M+1=273.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe cooled reaction mixture
  4. filtrationThe resulting solid was collected by vacuum filtration
  5. washwashed into a flask with EtOAc/MeOH
  6. customevaporated
  7. customdried

Sources & evidence

ORD record
ord-906f7f4657734bd284524fca4767005f
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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