Ethylene Glycol → HCID 86677765, compound

HRID 1499841Notes

Reaction equation

HRID 1499841 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[Cl:7][C:8]1[C:9]([CH3:36])=[C:10]([C:29]2[CH:30]=[N:31][C:32](F)=[CH:33][CH:34]=2)[C:11]([O:27][CH3:28])=[C:12]([CH:14]([N:16]2[C:20]3=[N:21][CH:22]=[N:23][C:24]([NH2:25])=[C:19]3[C:18]([CH3:26])=[N:17]2)[CH3:15])[CH:13]=1>>[NH2:25][C:24]1[N:23]=[CH:22][N:21]=[C:20]2[N:16]([CH:14]([C:12]3[C:11]([O:27][CH3:28])=[C:10]([C:29]4[CH:34]=[CH:33][C:32]([O:5][CH2:4][CH2:3][OH:6])=[N:31][CH:30]=4)[C:9]([CH3:36])=[C:8]([Cl:7])[CH:13]=3)[CH3:15])[N:17]=[C:18]([CH3:26])[C:19]=12

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 86677764HCID 86677764, compound

Product 1

HCID 86677765HCID 86677765, compoundYield 17%

Procedure

Sodium hydride (20 mg, 0.5 mmol) was added to 1,2-ethanediol (0.5 mL, 9 mmol) and the mixture was stirred at room temperature for 10 min. At this time 1-{1-[5-chloro-3-(6-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10 mg, 0.023 mmol) was added and then the reaction was stirred at 110° C. overnight. The crude was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (1.8 mg, 17%). The product was isolated as a single enantiomer. LCMS calculated for C23H26ClN6O3 (M+H)+: m/z=469.2; Found: 469.1.

Workup

  1. stirringthe reaction was stirred at 110° C. overnight
  2. customThe crude was purified
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-d18cb45415234f99a1b631841a8ff5c1
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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