Hydrochloric Acid → HCID 86696651, compound

HRID 1774149Notes

Reaction equation

HRID 1774149 reaction equation
Cl.[F:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=2)=[N:5][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:7][CH:8]=1.C([O-])(O)=[O:24].[Na+]>>[F:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][NH:19][C:18](=[O:24])[CH:17]=2)=[N:5][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86696652HCID 86696652, compound

Product 1

HCID 86696651HCID 86696651, compoundYield 97%

Procedure

1M HCl (15 mL) was added to 5-fluoro-4-(2-fluoropyridin-4-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-amine (0.26 g, 0.89 mmol). The suspension was heated at reflux. After 2.5 hours, the suspension was neutralized with NaHCO3, and the solid was collected by vacuum filtration. This was suspended in MeOH and evaporated to yield 4-(5-fluoro-2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.25 g, 0.86 mmol, 97% yield). 1H NMR (400 MHz, (CD3)2SO) δ 11.80 (br s, 1H), 8.48 (d, 1H), 7.52 (d, 1H), 7.40 (d, 1H), 6.83 (br s, 1H), 6.65-6.61 (m, 1H), 3.90-3.84 (m, 3H), 3.43-3.36 (m, 2H), 1.88-1.81 (m, 2H), 1.57-1.46 (m, 2H); m/z (APCI-pos) M+1=291.1.

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux
  3. filtrationthe solid was collected by vacuum filtration
  4. customevaporated

Sources & evidence

ORD record
ord-106f23e54c7a4c5bb676e83395cb07df
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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