Tetrabutylammonium Fluoride → HCID 58346552, compound

HRID 222031Notes

Reaction equation

HRID 222031 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][C:16]3[C:22]4=[C:23]([NH:27][C:28]5[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=6)=[C:30]([Cl:42])[CH:29]=5)[N:24]=[CH:25][N:26]=[C:21]4[S:20][C:17]=32)=[N:12]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:42][C:30]1[CH:29]=[C:28]([NH:27][C:23]2[C:22]3[C:16]4[CH2:15][CH2:14][C:13]5[C:18](=[CH:19][N:11]([CH2:10][CH2:9][OH:8])[N:12]=5)[C:17]=4[S:20][C:21]=3[N:26]=[CH:25][N:24]=2)[CH:33]=[CH:32][C:31]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58346671HCID 58346671, compound

Product 1

HCID 58346552HCID 58346552, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 80 mL THF cooled to 0° C. was added 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (2.40 g, 3.9 mmol). To the homogeneous mixture was then added TBAF in THF (1M, 4.3 mL). The dark contents were then stirred with warming to rt over a 1 h period, after which time the solvent was removed under reduced pressure. The crude residue was diluted with water (100 mL) and vigorously stirred. The precipitate formed was collected by filtration and further triturated with ethanol to afford the desired product (1.90 g, 92%) as a light-brown solid. 1H-NMR (DMSO-d6) δ 8.60 (d, 1H), 8.43 (s, 1H), 8.36 (s, 1H), 7.94 (s, 1H), 7.88 (td, 1H), 7.78 (d, 1H), 7.60 (d, 1H), 7.54 (dd, 1H), 7.38 (t, 1H), 7.24 (d, 1H), 5.29 (s, 2H), 4.94 (t, 1H), 4.12 (t, 2H), 3.74 (q, 2H), 3.39 (t, 2H), 2.93 (t, 2H); LCMS RT=2.32 min; [M+H]+=505.3.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. additionThe crude residue was diluted with water (100 mL)
  3. stirringvigorously stirred
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. customfurther triturated with ethanol

Sources & evidence

ORD record
ord-312fd6ab8bbb4f21ba03cdad3ceeb02e
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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