3,4-(Methylenedioxy)phenylmagnesium bromide solution → 9-(2-Benzo[1,3]dioxol-5-yl-2-hydroxy-propyl)-7,7-dimethyl-2-(pyrimidin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

HRID 505346Notes

Reaction equation

HRID 505346 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:18][N:6]2[C:7](=[O:17])[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][N:12]=3)[N:10]=[C:5]2[N:4]([CH2:19][C:20](=[O:22])[CH3:21])[CH2:3]1.[CH2:24]1[O:32][C:31]2[C:26](=[CH:27][CH:28]=[C-:29][CH:30]=2)[O:25]1.[Mg+2].[Br-]>O1CCCC1>[O:25]1[C:26]2[CH:27]=[CH:28][C:29]([C:20]([OH:22])([CH3:21])[CH2:19][N:4]3[C:5]4=[N:10][C:9]([C:11]5[CH:16]=[CH:15][N:14]=[CH:13][N:12]=5)=[CH:8][C:7](=[O:17])[N:6]4[CH2:18][C:2]([CH3:1])([CH3:23])[CH2:3]3)=[CH:30][C:31]=2[O:32][CH2:24]1

Participants

4

Reactant 2

HCID 44296443,4-(Methylenedioxy)phenylmagnesium bromide solutionHCID 178510677,7-Dimethyl-9-(2-oxo-propyl)-2-(pyrimidin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 101378429-(2-Benzo[1,3]dioxol-5-yl-2-hydroxy-propyl)-7,7-dimethyl-2-(pyrimidin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.3 g (0.957 mmol) of 7,7-dimethyl-9-(2-oxo-propyl)-2-(pyrimidin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one in 2 ml of anhydrous tetrahydrofuran at −2° C. was added 2.1 ml (9.57 mmol) of a solution of 3,4-(methylenedioxy)phenylmagnesiumbromide (1M solution in tetrahydrofuran/toluene 50/50) during 20 min. After stirring for 15 min. at room temperature the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with dichloromethane and the extracts washed with a saturated aqueous solution of sodium chloride, dried and evaporated. The residue was purified by chromatography on silica gel eluting with a mixture of ethyl acetate/cyclohexane in the proportions 50/50 to 100/0 to give 0.210 g (50%) of product. Mp.: 194-196° C.

Workup

  1. customwas quenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washthe extracts washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with a mixture of ethyl acetate/cyclohexane in the proportions 50/50 to 100/0

Sources & evidence

ORD record
ord-471765dd31364a40b89b34267cced7c2
Source dataset
uspto-grants-2010_08
Patent number
US07781440B2

Reaction notes

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