3-Methylbenzyl alcohol → HCID 90403107, compound

HRID 2200663Notes

Reaction equation

[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].Br[C:13]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:20]2[C:19](=[O:30])[N:18]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][O:38]3)[C:17](=[O:43])[N:16]([CH3:44])[C:15]=2[N:14]=1.[Cl-].[NH4+]>CN(C=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:21]2[C:20]3[C:19](=[O:30])[N:18]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH:37]4[CH2:42][CH2:41][CH2:40][CH2:39][O:38]4)[C:17](=[O:43])[N:16]([CH3:44])[C:15]=3[N:14]=[C:13]2[O:8][CH2:7][C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:9])[CH:2]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of m-tolylmethanol (37 mg, 0.3 mmol) in DMF (2 mL) was added sodium hydride (18 mg, 0.45 mmol) at 0° C. After stirring at 0° C. for 30 min, 8-bromo-7-(4-chlorobenzyl)-3-methyl-1-(2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)ethyl)-1H-purine-2,6(3H,7H)-dione (80 mg, 0.15 mmol, intermediate 11) was added. The mixture was stirred at 0° C. for 15 min, then aqueous ammonium chloride solution (2 mL) was added at 0° C. The mixture was partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give a crude product which was used without purification. LCMS retention time 1.967 min; LCMS MH+-THP 499.

Workup

stirringThe mixture was stirred at 0° C. for 15 min
customThe mixture was partitioned between ethyl acetate and water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1a35f95b76844e119fc364ef29d7040b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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