Potassium Carbonate → HCID 59526227, compound

HRID 386146Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.[NH2:15][C:16]1[S:17][C:18]([C:24]2[N:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:25]=2)=[CH:19][C:20]=1[C:21]([NH2:23])=[O:22].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:9]1([CH2:8][C:4]2[N:3]=[C:2]([NH:15][C:16]3[S:17][C:18]([C:24]4[N:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:25]=4)=[CH:19][C:20]=3[C:21]([NH2:23])=[O:22])[CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-[(4-Chloropyrimidin-2-yl)methyl]morpholine (Example 529 Step 1) (85 mg, 0.40 mmol), 2-amino-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)thiophene-3-carboxamide (Intermediate 40) (142 mg, 0.42 mmol), Pd2 dba3 (36 mg, 0.040 mmol), X-Phos (95 mg, 0.20 mmol), and K2CO3 (61 mg, 0.44 mmol) were combined in a vial, sealed, and evacuated/backfilled with nitrogen. Degassed t-amyl alcohol (1.0 mL) was added, and the reaction was vigorously stirred at 100° C. overnight. The reaction mixture was then diluted with MeOH, combined with silica, and evaporated. Flash chromatography (dry load, 0-15% MeOH/EtOAc) afforded the title compound as an orange solid.

Workup

customsealed
customevacuated/backfilled with nitrogen
additionDegassed t-amyl alcohol (1.0 mL) was added
additionThe reaction mixture was then diluted with MeOH
customevaporated
dry with materialFlash chromatography (dry load, 0-15% MeOH/EtOAc)

Sources & evidence

ORD record: ord-d5dbaa7b77414c2cbb49a593a17d0049
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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