Tetrabutylammonium Fluoride → 2-(2-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol

HRID 2262294Notes

Reaction equation

HRID 2262294 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[S:8][C:6]=2[N:7]=1.[CH3:21][C:22]1[N:39](COCC[Si](C)(C)C)[C:25]2=[N:26][CH:27]=[C:28](C3OC(C)(C)C(C)(C)O3)[CH:29]=[C:24]2[N:23]=1.C[Si](C)(C)CCOCN1C2C=C(C3N=C(N4CCOCC4)C4C=C(C(O)(C)C)SC=4N=3)C=CC=2N=C1C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:21][C:22]1[NH:39][C:25]2=[N:26][CH:27]=[C:28]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[S:8][C:6]=4[N:7]=3)[CH:29]=[C:24]2[N:23]=1

Participants

6

Reactant 4

HCID 2724141Tetrabutylammonium FluorideHCID 595930002-Methyl-6-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridineHCID 671915862-(2-(1-((2-(trimethylsilyl)ethoxy)methyl)-2-methyl-1H-benzo[d]imidazol-6-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-olHCID 866184422-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol

Product 1

HCID 1784320852-(2-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-olYield 3.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol (100 mg) was reacted with 161 mg of 3-((2-(trimethylsilyl)ethoxy)methyl)-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo[4,5-b]pyridine 54 via Example 6b and General Procedure A. Crude 2-(2-(1-((2-(trimethylsilyl)ethoxy)methyl)-2-methyl-1H-benzo[d]imidazol-6-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol was then refluxed overnight with 2 equivalents of tetrabutylammoniumfluoride in THF to remove the SEM protecting group. The crude material was then extracted with water and ethyl acetate. The organic layer was concentrated to dryness and then purified via reverse phase HPLC to give 5.1 mg of 414. MS (Q1) 411.2 (M)+

Workup

  1. customto remove the SEM
  2. extractionThe crude material was then extracted with water and ethyl acetate
  3. concentrationThe organic layer was concentrated to dryness
  4. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-85f02f7878cf494abd8e1dc6be60046c
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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