Tetrabutylammonium Fluoride → [(3aR,4R,6R,6aS)-6-({4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-6-methyl-1,3,5-triazin-2-yl}amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-methanol

HRID 1747614Notes

Reaction equation

HRID 1747614 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([NH:20][C:21]2[N:26]=[C:25]([NH:27][C@@H:28]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29]3)[N:24]=[C:23]([CH3:37])[N:22]=2)[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C@@H:28]1([NH:27][C:25]2[N:24]=[C:23]([CH3:37])[N:22]=[C:21]([NH:20][C@H:12]3[C@@H:13]4[O:17][C:16]([CH3:19])([CH3:18])[O:15][C@@H:14]4[C@@H:10]([CH2:9][OH:8])[CH2:11]3)[N:26]=2)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66797981N-[(3aS,4R,6S,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-N'-[(1S)-2,3-dihydro-1H-inden-1-yl]-6-methyl-1,3,5-triazine-2,4-diamine

Product 1

HCID 66798131[(3aR,4R,6R,6aS)-6-({4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-6-methyl-1,3,5-triazin-2-yl}amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-methanolYield 116%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-[(3aS,4R,6S,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-N′-[(1S)-2,3-dihydro-1H-inden-1-yl]-6-methyl-1,3,5-triazine-2,4-diamine (0.23 g, 0.00044 mol) in THF (1 mL) was added 1.00 M of TBAF in THF (1.31 mL). The reaction was stirred for 30 minutes. The solution was concentrated and the residue purified by flash chromatography (0 to 4% MeOH/EtOAc) to afford 210 mg (>99%) of the title compound. LC/MS: Rt=1.24 min, ES+ 412 (FA standard).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue purified by flash chromatography (0 to 4% MeOH/EtOAc)

Sources & evidence

ORD record
ord-326128e1caf54a66b80d48539be09102
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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