Potassium Carbonate → HCID 90403121, compound

HRID 2200580Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 8-(2-fluoro-5-(trifluoromethoxy)benzyl)-1-(4-methoxybenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (67 mg, 0.14 mmol) in DMF (3 mL) was added 1-(bromomethyl)-4-chlorobenzene (43.2 mg, 0.21 mmol) followed by potassium carbonate (38.7 mg, 0.28 mmol). The reaction was heated to 60° C. for 3 h. The reaction was partitioned between ethyl acetate and brine. The organic phase was dried and concentrated to give a crude product, which was purified by silica gel chromatography eluting with DCM/methanol (60:1) to give 7-(4-chlorobenzyl)-8-(2-fluoro-5-(trifluoromethoxy)benzyl)-1-(4-methoxybenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (71.2 mg, 84.3% yield) as a white solid. LCMS retention time 2.375 min; LCMS MH+ 603.

Workup

customThe reaction was partitioned between ethyl acetate and brine
customThe organic phase was dried
concentrationconcentrated
customto give a crude product, which
customwas purified by silica gel chromatography
washeluting with DCM/methanol (60:1)

Sources & evidence

ORD record: ord-00046495523f465d9faaa2991964b677
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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