Trifluoroacetic acid → [4-(3-aminophenoxy)-2-({1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol

HRID 577669Notes

Reaction equation

HRID 577669 reaction equation
[CH3:1][N:2]([CH3:43])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]2[N:12]=[C:13]([O:28][C:29]3[CH:30]=[C:31]([NH:35]C(=O)OC(C)(C)C)[CH:32]=[CH:33][CH:34]=3)[C:14]3[CH:19]=[CH:18][N:17]([CH2:20][O:21]CC[Si](C)(C)C)[C:15]=3[N:16]=2)[CH:7]=[N:6]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:35][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=1)[O:28][C:13]1[C:14]2[CH:19]=[CH:18][N:17]([CH2:20][OH:21])[C:15]=2[N:16]=[C:11]([NH:10][C:8]2[CH:7]=[N:6][N:5]([CH2:4][CH2:3][N:2]([CH3:43])[CH3:1])[CH:9]=2)[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679614HCID 86679614, compound

Product 1

HCID 86679613[4-(3-aminophenoxy)-2-({1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-{[2-({1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}amino)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy}phenyl)carbamate in DCM (5 mL) was added TFA (3 mL) and stirred at rt for 4 hrs. This was concentrated down to give the title compound as a dark oil that was taken on to the next step with no purification. m/z (ESI+) for O20H24N8O2 409.1 (M+H)+.

Workup

  1. concentrationThis was concentrated down

Sources & evidence

ORD record
ord-0c18d2fedc4e4bbcb754874ab04d50cf
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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