Sodium t-butoxide → HCID 178489900, compound

HRID 912108Notes

Reaction equation

HRID 912108 reaction equation
Br(O)(=O)=O.[O:5]1[CH2:10][CH2:9][N:8]([C:11]([NH2:13])=[NH:12])[CH2:7][CH2:6]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:28]=[CH:29][CH:30]=1)[C:19]([CH:21]1[CH2:26][CH:25]=C[O:23][C:22]1=O)=O.CC(C)([O-:34])C.[Na+]>CC(O)(C)C>[OH:34][CH2:25][CH2:26][C:21]1[C:22]([OH:23])=[N:12][C:11]([N:8]2[CH2:9][CH2:10][O:5][CH2:6][CH2:7]2)=[N:13][C:19]=1[C:18]1[CH:28]=[CH:29][CH:30]=[C:16]([O:15][CH3:14])[CH:17]=1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 67385413HCID 67385413, compoundHCID 86640118HCID 86640118, compound

Product 1

HCID 178489900HCID 178489900, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Morpholinoformamidine bromate salt (200 mg, 0.952 mmol), 3-(3-methoxybenzoyl)dihydropyran-2-one (544 mg, 3.6 mmol) and sodium t-butoxide (230 mg, 2.32 mmol) were added into a microwave reaction tube, and dissolved in t-BuOH (3 ml). After irradiation of microwave (200 W, 120° C.) for 1 hour, the solvent was removed under reduced pressure, to obtain a crude product as a brown solid. This was purified by silica gel column chromatography (dichloromethane/methanol=95/5), to obtain 5-(2-hydroxyethyl)-6-(3-methoxyphenyl)-2-(morpholin-4-yl)-pyrimidin-4-ol and 4-(3-methoxyphenyl)-2-(morpholin-4-yl)-5,6-furo[2,3-d]pyrimidine as colorless solid (Yield 16%).

Workup

  1. customAfter irradiation of microwave (200 W, 120° C.) for 1 hour
  2. customthe solvent was removed under reduced pressure
  3. customto obtain a crude product as a brown solid
  4. customThis was purified by silica gel column chromatography (dichloromethane/methanol=95/5)

Sources & evidence

ORD record
ord-598169932eaa452e8ca7d33c8c4a77e7
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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