4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one → HCID 67264859, compound

HRID 1685202Notes

Reaction equation

HRID 1685202 reaction equation
Cl.Cl.Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[N:14]([CH2:16][C:17]([N:20]([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:15]=2)=[CH:7][C:6]=1[C:29]([F:32])([F:31])[F:30].[Cl:33][C:34]1[C:35]2[CH2:42][C:41](=[O:43])[NH:40][C:36]=2[N:37]=[CH:38][N:39]=1>CN(C=O)C>[ClH:33].[CH3:22][N:20]([CH3:21])[C:17]([CH3:19])([CH3:18])[CH2:16][N:14]1[CH:15]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([F:4])=[C:6]([C:29]([F:30])([F:31])[F:32])[CH:7]=2)[N:12]=[C:13]1[CH:23]1[CH2:28][CH2:27][N:26]([C:34]2[C:35]3[CH2:42][C:41](=[O:43])[NH:40][C:36]=3[N:37]=[CH:38][N:39]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 86641617HCID 86641617, compound

Product 1

HCID 67264859HCID 67264859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine {2-[4-(4-fluoro-3-trifluoromethyl-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-1,1-dimethyl-ethyl}-dimethylamine tris hydrochloride (247 μmol; 200 mg); 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (1.5 equiv; 575 μmol; 97.5 mg); TEA (1.92 mmol; 267 μL); DMF (2 mL) and heat in microwave reactor at 160° C. for 30 min. Evaporate and purify on 40 g silica gel with 2-7.5% MeOH/DCM to provide 137.3 mg (0.25 mmol; 66%) of the title compound as the free base. Dissolve in DCM/MeOH, add 1 equiv 1M HCl in ether and evaporate to provide 162.4 mg of the title compound. MS (ES+): m/z=546 (M+H).

Workup

  1. customEvaporate
  2. custompurify on 40 g silica gel with 2-7.5% MeOH/DCM

Sources & evidence

ORD record
ord-fbbf1f75ac5f48e2bdf13edc60a14e55
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

Loading…