Tetrabutylammonium Fluoride → HCID 86605360, compound

HRID 132527Notes

Reaction equation

HRID 132527 reaction equation
[Si]([O:18][CH2:19][N:20]1[C:28]([CH2:29][CH2:30][CH3:31])=[N:27][C:26]2[C:21]1=[N:22][C:23]([C:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[N:24][C:25]=2[NH:32][O:33][CH3:34])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:18][CH2:19][N:20]1[C:28]([CH2:29][CH2:30][CH3:31])=[N:27][C:26]2[C:21]1=[N:22][C:23]([C:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[N:24][C:25]=2[NH:32][O:33][CH3:34]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86605361HCID 86605361, compound

Product 1

HCID 86605360HCID 86605360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 44 (22 g, 30.0 mmol) is dissolved in THF (200 L) and treated with TBAF (1M in THF, 30.68 mL) and the reaction mixture is stirred at room temperature for 2 h followed by concentration. The residue is purified on a silica gel column using chloroform:methanol (100:0 to 90:10) as an eluent to give 10g (70%) of 45 as a white foam, mp 188° C.: 1H NMR (DMSO-d6): δ: 8.23 (s, 1 H), 7.89 (s, 1 H), 7.4-6.9 (m, 14 H), 5.01 (bs, 1 H), 4.36 (m, 1 H), 3.84 (m, 1 H), 3.71 (s, 3 H), 3.67 (m, 1 H, partially masked by CH3 peak), 1.90 (m, 2 H), 0.73 (t, J=7.3 Hz, 3H). IR (KBr, cm−1) 3408, 3313, 2966, 1715, 1605, 1469 and 1249.

Workup

  1. concentrationfollowed by concentration
  2. customThe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-98fc121f8ed84c56b02a9baabd92f675
Source dataset
uspto-grants-2008_06
Patent number
US07388002B2

Reaction notes

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