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

HRID 1943194Notes

Reaction equation

HRID 1943194 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>O1CCCC1>[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 tetrahydrofuran (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 hour. 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
  3. custom300 ml on a rotary evaporator
  4. customwas precipitated during this procedure)
  5. stirringthen was stirred vigorously while solid sodium hydrogen carbonate
  6. additionwas added in portions (caution: effervescence) until the mixture
  7. filtrationThe resulting yellow solid was collected by filtration with suction
  8. washwashed with water (2×20 ml)
  9. customair-dried

Sources & evidence

ORD record
ord-2f4e672dd495492c830f92ed643b7e05
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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