Hydrochloric Acid → 4-(1,3-Dihydroxypropan-2-yl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 420682Notes

Reaction equation

HRID 420682 reaction equation
CC1(C)[O:7][CH2:6][CH:5]([N:8]2[C:13](=[O:14])[CH:12]=[N:11][C:10]3[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[N:18][C:9]2=3)[CH2:4][O:3]1.Cl>C1COCC1>[OH:3][CH2:4][CH:5]([N:8]1[C:13](=[O:14])[CH:12]=[N:11][C:10]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[N:18][C:9]1=2)[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580017664-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 666584804-(1,3-Dihydroxypropan-2-yl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one (17.40 g, 59.7 mmol) was dissolved in THF (220 ml) to give a dark yellow solution. 1M HCl aq. (200 ml) was added (transient blue and green colours appeared in the solution) and the now light yellow solution was stirred at room temperature for 1 h. The mixture was concentrated to ca. 300 ml on a rotary evaporator using a cold water bath (some solid was precipitated during this procedure) then was stirred vigorously while solid sodium hydrogen carbonate was added in portions (caution: effervescence) until the mixture was ca. pH 8. The resulting yellow solid was collected by filtration with suction, washed with water (2×20 ml) and air-dried to give the title compound as an amorphous yellow solid (13.805 g, 91%).

Workup

  1. customto give a dark yellow solution
  2. concentrationThe mixture was concentrated to ca. 300 ml on a rotary evaporator
  3. customwas precipitated during this procedure)
  4. stirringthen was stirred vigorously while solid sodium hydrogen carbonate
  5. additionwas added in portions (caution: effervescence) until the mixture
  6. filtrationThe resulting yellow solid was collected by filtration with suction
  7. washwashed with water (2×20 ml)
  8. customair-dried

Sources & evidence

ORD record
ord-08df364d16d04dcfbf5a00e25e3d5a18
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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