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Tetrabutylammonium Fluoride → N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 921324
Notes
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Reaction equation

HRID 921324 reaction equation
[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[C:15]3[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:16]=3[N:17]=2)=[C:7]([O:42][CH3:43])[CH:6]=1)([CH3:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(N)CN>[CH3:4][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:40])[CH3:41])(=[O:37])=[O:38])[C:15]3[CH:20]=[CH:19][NH:18][C:16]=3[N:17]=2)=[C:7]([O:42][CH3:43])[CH:6]=1)([CH3:1])=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86668794N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Product 1

HCID 68166174N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 3301
Ethylenediamine
Solvent
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of compound N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine in THF (1 mL) was added tetrabutylammonium fluoride (TBAF) in THF (1.0 M, 3 mL) and ethylenediamine (0.1 mL). The solution was heated at 60° C. for 24 hrs. About 40% conversion was observed by HPLC monitoring. Volatile components were removed on rotavap and the residue was subjected to prep-HPLC purification. The desired product was determined by NMR to be contaminated with TBAF, which was removed by water wash (4 times). Evaporation of EtOAc gave the pure compound (14 mg). MS/ES+: m/z=514.

Workup

  1. customVolatile components were removed on rotavap
  2. customthe residue was subjected to prep-HPLC purification
  3. customwas removed by water
  4. washwash (4 times)
  5. customEvaporation of EtOAc

Sources & evidence

ORD record
ord-7ff640c87374445388c02ee9b048b583
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273077B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes