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 2098865Notes

Reaction equation

HRID 2098865 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-ol

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 tetrabutylammoniumfloride 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-40f1d1a244514bc5b3c7f78b4ff09a63
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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