Trifluoroacetic acid → N2-(1H-indazol-6-yl)-N4-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidine-2,4-diamine

HRID 1038863Notes

Reaction equation

[F:1][C:2]([F:33])([F:32])[CH2:3][NH:4][C:5]1[C:6]2[O:31][CH:30]=[CH:29][C:7]=2[N:8]=[C:9]([NH:11][C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[N:17][N:18]3COCC[Si](C)(C)C)=[CH:14][CH:13]=2)[N:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:18]1[C:19]2[C:15](=[CH:14][CH:13]=[C:12]([NH:11][C:9]3[N:10]=[C:5]([NH:4][CH2:3][C:2]([F:32])([F:33])[F:1])[C:6]4[O:31][CH:30]=[CH:29][C:7]=4[N:8]=3)[CH:20]=2)[CH:16]=[N:17]1

Participants

Conditions

Temperature: 30 °C

Procedure

N4-(2,2,2-trifluoroethyl)-N2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)furo[3,2-d]pyrimidine-2,4-diamine (1.08 g, 2.257 mmol) was dissolved in DCM (15 mL). TFA (10 mL, 130 mmol) was added. The resulting mixture was stirred at about 30° C. for about 6 h. The mixture was concentrated in vacuo. The residue was diluted with DCM (30 mL) and the pH was adjusted to about pH=9.0 with concentrated NH4OH. The solvents were removed under reduced pressure and the resulting mixture was purified by preparative-HPLC (Table 2, method w) to afford N2-(1H-indazol-6-yl)-N4-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidine-2,4-diamine (0.15 g, 19%): LC/MS (Table 2, Method h) Rt=1.79 min; MS m/z: 349 (M+H)+. Syk IC50=A

Workup

concentrationThe mixture was concentrated in vacuo
additionThe residue was diluted with DCM (30 mL)
customThe solvents were removed under reduced pressure
customthe resulting mixture was purified by preparative-HPLC (Table 2, method w)

Sources & evidence

ORD record: ord-df7f377fffaf40b99da5cab95b222624
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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