Potassium Carbonate → HCID 90402901, compound

HRID 2200717Notes

Reaction equation

HRID 2200717 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:6]=2[C:5](=[O:30])[NH:4][C:3]1=[O:31].CC1C=CC(S(O[CH2:43][CH2:44][CH:45]([OH:47])[CH3:46])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[OH:47][CH:45]([CH3:46])[CH2:44][CH2:43][N:4]1[C:5](=[O:30])[C:6]2[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 132043233-Hydroxybutyl 4-methylbenzenesulfonate2×HCID 90403182HCID 90403182, compound

Product 1

HCID 90402901HCID 90402901, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-methyl-7-(pyridin-2-ylmethyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (30 mg, 0.07 mmol) in DMF (1 mL) was added 3-hydroxybutyl 4-methylbenzenesulfonate (25.6 mg, 0.105 mmol, intermediate 33) followed by potassium carbonate (14.5 mg, 0.105 mmol) and a catalytic amount of TBAI. The reaction was stirred at 60° C. for 2 h. The reaction was partitioned between ethyl acetate and brine. The organic phase was dried and concentrated to give crude product, which was purified by preparative HPLC to give 1-(3-hydroxybutyl)-3-methyl-7-(pyridin-2-ylmethyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (11.2 mg, 32% yield) as white solid. 1H-NMR (CD3OD) δ 8.38-8.39 (d, 1H), 7.65-7.69 (t, 1H), 7.23-7.31 (m, 2H), 7.07-7.17 (m, 2H), 5.72 (s, 2H), 4.32 (s, 2H), 4.01-4.11 (m, 2H), 3.75-3.77 (m, 1H), 3.58 (s, 3H), 1.71-1.75 (m, 2H), 1.17-1.19 (d, 3H). LCMS retention time 2.480 min; LCMS MH+ 504.

Workup

  1. customThe reaction was partitioned between ethyl acetate and brine
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customto give crude product, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-413a20b3552749669e84dd8294b2f3a4
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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