Dichloromethane → 4-(methoxy(phenyl)methyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine

HRID 1930629Notes

Reaction equation

[CH3:1][O:2][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][O:8][CH2:7]1)=O.[CH3:19][C:20]1[N:21]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH2:34])=[NH:33])=[CH:27][CH:26]=2)[CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CCO.O>[CH3:1][O:2][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]1[C:6]2[CH2:7][O:8][CH2:9][CH2:10][C:11]=2[N:34]=[C:32]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([N:21]3[CH:22]=[CH:23][N:24]=[C:20]3[CH3:19])=[CH:26][CH:27]=2)[N:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3-(2-Methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-one (100 mg, 0.40 mmol), 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (Example 41c) (87 mg, 0.40 mmol) and potassium carbonate (55.7 mg, 0.40 mmol) was slurrified in EtOH (4 mL) and heated to 50° C. for 15 h. DCM and water were added. The organic phase was separated, dried with MgSO4 concentrated and purified by preparative HPLC yielding 4-(methoxy(phenyl)methyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine (10.0 mg, 5.7%). MS (ES+) m/z 428.1 (M+H)+

Workup

customThe organic phase was separated
dry with materialdried with MgSO4
concentrationconcentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-7174aacd179b4c88ac353990dec18109
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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