Potassium Carbonate → HCID 178507930, compound

HRID 387455Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:10][C:11]([C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:36]1[CH:41]=[C:40]([NH2:42])[N:39]=[C:38]([NH2:43])[N:37]=1.[C:44]([O-:47])([O-])=[O:45].[K+].[K+]>CN(C=O)C.CO>[F:22][C:21]([F:24])([F:23])[C:44]([OH:47])=[O:45].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:10][C:11]([C:14]3[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=3)[O:20][C:36]3[N:37]=[C:38]([NH2:43])[N:39]=[C:40]([NH2:42])[CH:41]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 80 °C

Procedure

3-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H[1,2,4]triazol-3-yl]-phenol (100 mg, 0.282 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial. Solid potassium bis(trimethylsilyl)amide (140.6 mg, 0.705 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 4-chloro-2,6-diamino-pyrimidine (44.8 mg, 0.31 mmol) was added, followed by anhydrous K2CO3 (19.5 mg, 0.141 mmol). Then the vial was capped and microwaved at 250° C. for 20 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. The product was isolated as a TFA salt (37.8 mg of beige solid).

Workup

customThen the vial was capped
custommicrowaved at 250° C. for 20 min
filtrationfiltered through 0.22 um syringe
filtrationfilter
custompurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA

Sources & evidence

ORD record: ord-608d3a3fc16e4a988ad7bd9b061d42a8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372971B2

Reaction notes

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