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

HRID 1930695Notes

Reaction equation

HRID 1930695 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:27][C:28]([CH:30]2[C:35](=O)[CH2:34][CH2:33][O:32][CH2:31]2)=O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:18]=[C:28]([CH2:27][C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH3:19])[CH:22]=3)[C:30]3[CH2:31][O:32][CH2:33][CH2:34][C:35]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 593337883-(2-(3-methoxyphenyl)acetyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227, compound

Product 1

HCID 59333799N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-(3-methoxybenzyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amineYield 6.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (85 mg, 0.35 mmol), 3-(2-(3-methoxyphenyl)acetyl)dihydro-2H-pyran-4(3H)-one (86 mg, 0.35 mmol) and potassium carbonate (47.9 mg, 0.35 mmol) in ethanol (2 mL) were heated to 60° C. over night. DCM and water were added and the organic phase was separated and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC yielding N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-(3-methoxybenzyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine (10.00 mg, 6%).

Workup

  1. customthe organic phase was separated
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8af0c915234f4d419e86b757bd802483
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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