Sodium t-butoxide → HCID 178489900, compound

HRID 912075Notes

Reaction equation

HRID 912075 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:27]=[CH:28][CH:29]=1)[C:19]([CH:21]1[CH2:25][CH2:24][O:23][C:22]1=[O:26])=O.CC(C)([O-])C.[Na+]>C(O)(C)(C)C>[OH:23][CH2:24][CH2:25][C:21]1[C:22]([OH:26])=[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:27]=[CH:28][CH:29]=[C:16]([O:15][CH3:14])[CH:17]=1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 59244973HCID 59244973, 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)-dihydrofuran-2-one (419 mg, 1.904 mmol) and sodium t-butoxide (183 mg, 1.904 mmol) were added into a microwave reaction tube, followed by being dissolved in t-butanol (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. The crude was purified by silica gel column chromatography (DCM/MeOH=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.

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. customThe crude was purified by silica gel column chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-6278030739ef4faab52a304efb6f0635
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

Loading…