Hydrochloric Acid → 5-(((1-methyl-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidin-8-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile

HRID 920362

Reaction equation

HRID 920362 reaction equation
Cl[C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1.[OH:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)=[C:20]([CH:23]=1)[C:21]#[N:22].[H-].[Na+].Cl>CN(C)C=O>[CH3:11][N:7]1[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=[C:2]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=4)=[C:20]([CH:23]=3)[C:21]#[N:22])[CH:12]=[C:6]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 668254365-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrileHCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

Product 1

HCID 712367885-(((1-methyl-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidin-8-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrileYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (31 mg, 0.153 mmol) and 5-(hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (49.4 mg, 0.168 mmol) in N, N-dimethylformamide (DMF) (1.5 mL), was added NaH (18.36 mg, 0.459 mmol). The reaction mixture was stirred at rt for 30 min. Aqueous HCl solution was added to adjust pH to ˜7. Purification by Mass Directed AutoPrep (MDAP) afforded the title compound as a white solid (35 mg, 50% yield).

Workup

  1. customPurification by Mass Directed AutoPrep (MDAP)

Sources & evidence

ORD record
ord-0c9e5201ecb743db9072ce8594cefd05
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Linked notes

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