Hydrochloric Acid → HCID 86696651, compound

HRID 2365795Notes

Reaction equation

HRID 2365795 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-88505d993e1f44e884c68b627f1f60f6
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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