Dimethyl Sulfoxide → 3-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal

HRID 1426634Notes

Reaction equation

HRID 1426634 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([CH:16]([N:20]2[CH:24]=[C:23]([C:25]3[C:26]4[CH:33]=[CH:32][N:31]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:27]=4[N:28]=[CH:29][N:30]=3)[CH:22]=[N:21]2)[CH2:17][CH2:18][OH:19])[CH2:15][CH2:14][CH2:13][CH2:12]1.O>C(Cl)Cl>[CH:11]1([CH:16]([N:20]2[CH:24]=[C:23]([C:25]3[C:26]4[CH:33]=[CH:32][N:31]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:39])([CH3:41])[CH3:40])[C:27]=4[N:28]=[CH:29][N:30]=3)[CH:22]=[N:21]2)[CH2:17][CH:18]=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 574780333-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propan-1-ol

Product 1

HCID 574780313-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanalYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (0.108 mL, 1.28 mmol) in DCM (10.0 mL) at −78° C. was added DMSO (151 μL, 2.13 mmol). After stirring for 5 minutes, 3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propan-1-ol (471 mg, 1.07 mmol) in DCM (3.00 mL) was added. The mixture was stirred for 30 minutes at −78° C. TEA (594 μL, 4.26 mmol) was then added. The resulting mixture was then allowed to warm to room temperature over the course of 30 minutes. Water was added, and the layers were separated. The organic layer was washed successively with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine, and was then dried over sodium sulfate and the solvent was removed in vacuo. Flash column chromatography (eluting with a gradient of 0-60% ethyl acetate in hexanes) afforded the product (384 mg, 82%).

Workup

  1. stirringThe mixture was stirred for 30 minutes at −78° C
  2. customthe layers were separated
  3. washThe organic layer was washed successively with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine
  4. dry with materialwas then dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. washFlash column chromatography (eluting with a gradient of 0-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3dd08e604ff749ae850efa57d2c6b1c6
Source dataset
uspto-grants-2015_01
Patent number
US08933086B2

Reaction notes

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