Magnesium Bromide → (5-hydroxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

HRID 1162206Notes

Reaction equation

HRID 1162206 reaction equation
[Br-].[Mg+2].[Br-].[C:4]([O:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[O:23]C)[N:14]=[CH:13]1)(=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6]>N1C=CC=CC=1>[C:4]([O:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[OH:23])[N:14]=[CH:13]1)(=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 82241Magnesium BromideHCID 68496089(5-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Product 1

HCID 68496163(5-hydroxy-4-oxoquinazolin-3(4H)-yl)methyl pivalateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

Magnesium bromide (7 g, 38 mmol) was added to a solution of (5-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate (7.4 g, 25.5 mmol) in pyridine (25 ml). The mixture was stirred at 120° C. for one hour. After cooling, the solvents were evaporated under high vacuum. Diluted acetic acid (15 ml in 100 ml water) was added. The precipitated solid was filtered, washed with water and dried under high vacuum in the presence of P2O5 to give (5-hydroxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate as a white solid (6.33 g, 90%); NMR Spectrum (CDCl3) 1.23 (s, 9H), 5.93 (s, 2H), 6.99 (d, 1H), 7.22 (d, 1H), 7.68 (t, 1H), 8.21 (s, 1H); Mass spectrum MH+ 277.

Workup

  1. temperatureAfter cooling
  2. customthe solvents were evaporated under high vacuum
  3. additionDiluted acetic acid (15 ml in 100 ml water) was added
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. dry with materialdried under high vacuum in the presence of P2O5

Sources & evidence

ORD record
ord-b8c087fcad29492e82b2efb28a7aa7e8
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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