Potassium Carbonate → 8-(cyclopentyloxy)-3-methyl-7-((4-methylthiazol-2-yl)methyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200680Notes

Reaction equation

[CH:1]1([O:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:11](=[O:27])[N:10]([CH3:28])[C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:30][C:31]1[S:32][CH:33]=[C:34]([CH3:36])[N:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH:1]1([O:6][C:7]2[N:15]([CH2:30][C:31]3[S:32][CH:33]=[C:34]([CH3:36])[N:35]=3)[C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:11](=[O:27])[N:10]([CH3:28])[C:9]=3[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-(cyclopentyloxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (0.12 g, 0.31 mmol) in DMF (5 mL) was added 2-(chloromethyl)-4-methylthiazole (91 mg, 0.62 mmol, intermediate 54), potassium carbonate (85 mg, 0.62 mmol), and TBAI (2 mg, 0.02 mmol). The reaction was heated at 50° C. overnight. The mixture was cooled and partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was used without purification. LCMS retention time 1.704 min; LCMS MH+-THP 470.

Workup

temperatureThe mixture was cooled
custompartitioned between ethyl acetate and water
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a119737ef4d248ff98d667da65813883
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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