Triethylsilane → HCID 178429378, compound

HRID 707375Notes

Reaction equation

HRID 707375 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([NH:9][C@H:10]3[CH2:13][C@H:12]([N:14]4[C:18]5[N:19]=[C:20](SC)[N:21]=[CH:22][C:17]=5[C:16]([CH3:26])([CH3:25])[C:15]4=[O:27])[CH2:11]3)[S:8][C:4]=2[CH:3]=1.C([SiH](CC)CC)C>O1CCCC1.[Pd]>[F:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([NH:9][C@H:10]3[CH2:11][C@H:12]([N:14]4[C:18]5[N:19]=[CH:20][N:21]=[CH:22][C:17]=5[C:16]([CH3:25])([CH3:26])[C:15]4=[O:27])[CH2:13]3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 12052Triethylsilane3×HCID 178503400HCID 178503400, compound

Product 1

HCID 178429378HCID 178429378, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

7-(Trans-3-((6-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-5,5-dimethyl-2-(methylthio)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (EXAMPLE 156) (0.200 g, 0.466 mmol) was dissolved in dry tetrahydrofuran (10 mL) under nitrogen. Palladium (10 wt. % on activated carbon, 0.080 g, 0.075 mmol) was added followed by triethylsilane (0.200 ml, 1.252 mmol). The suspension was stirred at room temperature. After 40 minutes additional triethylsilane (0.5 mL) was added and the reaction stirred for another 4 hours. Additional palladium/carbon (0.122 g) and triethylsilane (0.25 mL) were added and the reaction stirred for another 55 minutes. The mixture was filtered through a pad of CELITE® and evaporated to dryness under reduced pressure. Purification using silica chromatography (0-5% methanol in dichloromethane gradient) gave 7-(trans-3-((6-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.091 g, 0.237 mmol, 51.0% yield) as a white solid. m/z: 384.0 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 1.42 (s, 6H) 2.42-2.53 (m, 2 H) 3.38-3.53 (m, 2 H) 4.55-4.65 (m, 1 H) 5.15-5.27 (m, 1 H) 7.03 (td, J=9.0 Hz, 2.6 Hz, 1H) 7.32 (dd, J=8.2 Hz, 2.6 Hz, 1H) 7.49 (dd, J=8.9 Hz, 4.7 Hz, 1H) 8.33 (s, 1H) 8.84 (s, 1H).

Workup

  1. stirringthe reaction stirred for another 4 hours
  2. stirringthe reaction stirred for another 55 minutes
  3. filtrationThe mixture was filtered through a pad of CELITE®
  4. customevaporated to dryness under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-4d8509bcf39c45a2bb26061419c8b989
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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