Sodium hydride → 1-(4-chlorobenzyl)-8-((3,4-difluorobenzyl)oxy)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 930806Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:6]2[NH:7][CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:12])[N:3]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.[F:24][C:25]1[CH:26]=[C:27]([CH2:32][OH:33])[CH:28]=[CH:29][C:30]=1[F:31]>CN(C)C=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:7]2[CH2:8][CH2:9][CH2:10][N:5]3[C:4](=[O:12])[N:3]=[C:2]([O:33][CH2:32][C:27]4[CH:28]=[CH:29][C:30]([F:31])=[C:25]([F:24])[CH:26]=4)[CH:11]=[C:6]23)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (50 mg, 0.27 mmol) and sodium hydride (23.70 mg, 0.59 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added a solution of 1-(bromomethyl)-4-chlorobenzene (66.4 mg, 0.32 mmol) in anhydrous N,N-dimethylformamide (1 ml) at r.t, and then stirred for 1 h at 50° C. Then, a solution of (3,4-difluorophenyl) methanol (46.6 mg, 0.32 mmol) in N, N-dimethylformamide (1 ml) was added and stirred for 1 h at r.t. The reaction mixture was quenched by water. Purification via reverse phase column using acetonitrile/water as eluent afforded the title compound (13 mg).

Workup

stirringstirred for 1 h at r.t
customThe reaction mixture was quenched by water
customPurification via reverse phase column

Sources & evidence

ORD record: ord-6ad26c5925c8422cb6e215c8d8935e4b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296755B2

Reaction notes

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