Potassium Carbonate → HCID 68859860, compound

HRID 1783499Notes

Reaction equation

HRID 1783499 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]3)[N:7]([CH2:25][C:26]#[C:27][CH3:28])[C:6]=2[C:5](=[O:29])[NH:4][C:3]1=[O:30].[O:31]1[CH:35]=[CH:34][C:33]([CH2:36]O)=[CH:32]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[O:31]1[CH:35]=[CH:34][C:33]([CH2:36][N:4]2[C:5](=[O:29])[C:6]3[N:7]([CH2:25][C:26]#[C:27][CH3:28])[C:8]([N:11]4[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:12]4)=[N:9][C:10]=3[N:2]([CH3:1])[C:3]2=[O:30])=[CH:32]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 204493-FuranmethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11546173Linagliptin Impurity D

Product 1

HCID 68859860HCID 68859860, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 300 mg of 3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine, 95 μl furan-3-yl-methanol, 302 mg triphenylphosphine and 226 μl diisopropyl azodicarboxylate in 4 ml tetrahydrofuran is stirred overnight at ambient temperature. For working up the reaction mixture is combined with saturated potassium carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate and evaporated down. The flask residue is chromatographed over a silica gel column with cyclohexane/ethyl acetate (1:1 to 3:7).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. customevaporated down
  4. customThe flask residue is chromatographed over a silica gel column with cyclohexane/ethyl acetate (1:1 to 3:7)

Sources & evidence

ORD record
ord-6f2754fdc83c48d2944769c8515ade70
Source dataset
uspto-grants-2009_03
Patent number
US07501426B2

Reaction notes

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