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Water → 5-Chloro-2-{4-[(S)-2-hydroxy-1-(2-methyl-pyrimidin-5-yl)-ethylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

HRID 657814
Notes
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Reaction equation

HRID 657814 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:18][C:19]1[C:20]2[CH2:28][N:27]([C:29]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:30]=3[C:31]#[N:32])[CH2:26][CH2:25][C:21]=2[N:22]=[CH:23][N:24]=1)[C:11]1[CH:12]=[N:13][C:14]([CH3:17])=[N:15][CH:16]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O.CCOC(C)=O>C1COCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:29]([N:27]2[CH2:26][CH2:25][C:21]3[N:22]=[CH:23][N:24]=[C:19]([NH:18][C@@H:10]([C:11]4[CH:16]=[N:15][C:14]([CH3:17])=[N:13][CH:12]=4)[CH2:9][OH:8])[C:20]=3[CH2:28]2)=[C:30]([CH:33]=1)[C:31]#[N:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 69177698(S)-2-(4-(2-(tert-butyldimethylsilyloxy)-1-(2-methylpyrimidin-5-yl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-chlorobenzonitrile

Product 1

HCID 250606025-Chloro-2-{4-[(S)-2-hydroxy-1-(2-methyl-pyrimidin-5-yl)-ethylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-2-(4-(2-(tert-butyldimethylsilyloxy)-1-(2-methylpyrimidin-5-yl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-chlorobenzonitrile (60 mg, 0.11 mmol) in THF (10 mL) was added 1M TBAF in THF (5 mL). The reaction mixture was stirred at room temperature for 10 minutes, and then treated with water and EtOAc. The organic layer was washed with aq. NaHCO3 and brine, dried (MgSO4), and concentrated. The residue was washed by ethyl ether and water (to completely remove TBAF) and dried to yield the final product as a light colored solid.

Workup

  1. washThe organic layer was washed with aq. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washThe residue was washed by ethyl ether and water (to completely remove TBAF) and
  5. customdried

Sources & evidence

ORD record
ord-63c765792fe6423eaf10ba215662d1c1
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08076345B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes