Tetrabutylammonium Fluoride → HCID 178519977, compound

HRID 2169449Notes

Reaction equation

HRID 2169449 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:44]1[CH2:46][CH2:45]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([N:35]3[C:39]4=[N:40][CH:41]=[CH:42][CH:43]=[C:38]4[CH:37]=[CH:36]3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:44]1([N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([N:35]4[C:39]5=[N:40][CH:41]=[CH:42][CH:43]=[C:38]5[CH:37]=[CH:36]4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:46][CH2:45]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455282HCID 178455282, compound

Product 1

HCID 178519977HCID 178519977, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (417) (96 mg, 0.15 mmol) in tetrahydrofuran (3 mL) was added tetrabutylammoniumfluoride 1M in tetrahydrofuran (0.7 mL, 0.75 mmol) at room temperature and stirring was continued for 1 h. The tetrahydrofuran was removed from the reaction mixture, diluted with ethyl acetate (50 mL) and washed with water (2×30 mL) and brine (30 mL). The organic phase was thereafter dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid cyclopropyl-(2-hydroxyethyl)-amide (418) (60 mg, crude) as an off-white sticky solid.

Workup

  1. customThe tetrahydrofuran was removed from the reaction mixture
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with water (2×30 mL) and brine (30 mL)
  4. customThe organic phase was thereafter dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6818ebf9a77465aa701db43b7236f15
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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