Dichloromethane → HCID 46199429, compound

HRID 1930632Notes

Reaction equation

HRID 1930632 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([CH:10]2[C:15](=O)[CH2:14][CH2:13][O:12][CH2:11]2)=O)[CH2:3][CH2:2]1.[CH3:17][C:18]1[N:19]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=2)[CH:20]=[CH:21][N:22]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CCO.O>[CH3:17][C:18]1[N:19]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30]3[N:31]=[C:8]([CH2:7][CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[C:10]4[CH2:11][O:12][CH2:13][CH2:14][C:15]=4[N:32]=3)=[CH:27][CH:28]=2)[CH:20]=[CH:21][N:22]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 59333736HCID 59333736, compoundHCID 178432900HCID 178432900, compound

Product 1

HCID 46199429HCID 46199429, compoundYield 4.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

3-(2-(Tetrahydro-2H-pyran-4-yl)acetyl)dihydro-2H-pyran-4(3H)-one (200 mg, 0.88 mmol), 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (190 mg, 0.88 mmol, Example 41c) and potassium carbonate (122 mg, 0.88 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 and the solvent was evaporated. The crude product was purified using preparative HPLC yielding N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-4-((tetrahydro-2H-pyran-4-yl)methyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine (15.0 mg, 4.0%).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried with MgSO4
  3. customthe solvent was evaporated
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-afc52013b9db494cb80cab5b767c95e1
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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