Methanol → HCID 18936859, compound

HRID 357124Notes

Reaction equation

HRID 357124 reaction equation
C([N:8]1[C:17](=[O:18])[C:16]([CH:19]([CH3:21])[CH3:20])=[C:11]2[S:12][CH2:13][CH2:14][CH2:15][N:10]2[C:9]1=[O:22])C1C=CC=CC=1.B(Br)(Br)Br.CO>C1(C)C=CC=CC=1>[CH:19]([C:16]1[C:17](=[O:18])[NH:8][C:9](=[O:22])[N:10]2[CH2:15][CH2:14][CH2:13][S:12][C:11]=12)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18936839HCID 18936839, compound

Product 1

HCID 18936859HCID 18936859, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4.75 g (15 mmol) of 7-benzyl-9-isopropyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione in 120 ml of toluene, 7.52 g (30 mmol) of boron tribromide was added under ice cooling conditions, followed by refluxing for 16 hours. After the reaction mixture was cooled, 50 ml of methanol was added, followed by stirring for 30 minutes. After this mixture was concentrated to dryness, methanol-diethyl ether was added to the residue. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to yield 1.95 g (57.4%, light white powder) of the desired product.

Workup

  1. temperatureby refluxing for 16 hours
  2. temperatureAfter the reaction mixture was cooled
  3. concentrationAfter this mixture was concentrated to dryness, methanol-diethyl ether
  4. additionwas added to the residue
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-7529b94de67b47009c567fa48a979585
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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