Potassium Carbonate → HCID 137108693, compound

HRID 60770Notes

Reaction equation

HRID 60770 reaction equation
C([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([CH2:16][C:17]([CH3:19])=[CH2:18])[C@H:13]([N:20]2[C:24]3[N:25]=[C:26]([NH2:30])[NH:27][C:28](=[O:29])[C:23]=3[S:22][C:21]2=[O:31])[O:12]1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:30][C:26]1[NH:27][C:28](=[O:29])[C:23]2[S:22][C:21](=[O:31])[N:20]([C@H:13]3[C@H:14]([CH2:16][C:17]([CH3:19])=[CH2:18])[CH2:15][C@@H:11]([CH2:10][OH:9])[O:12]3)[C:24]=2[N:25]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 137108731[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-(2-methylallyl)tetrahydrofuran-2-yl]methyl benzoate2×

Product 1

HCID 137108693HCID 137108693, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-(2-methylallyl)tetrahydrofuran-2-yl]methyl benzoate (compound 41b, 180 mg, 0.41 mmol) in methanol was stirred with K2CO3 (150 mg, 1.09 mmol) at room temperature for 4 hours. The reaction was quenched by addition of acetic acid and the resulting mixture was concentrated in vacuo. The residue was purified by preparative HPLC to afford 41 mg of 3-[(2R,3R,5S)-3-allyl-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-amino-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 41) as a white powder.

Workup

  1. customThe reaction was quenched by addition of acetic acid
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b9b737dda1954cb399f80eb2f497c72b
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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