Potassium Hydroxide → HCID 136344411, compound

HRID 1022448Notes

Reaction equation

HRID 1022448 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[OH-:20].[K+]>O1CCCC1>[Cl:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 219764212,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 136344411HCID 136344411, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (336.5 mg, 1.06 mmol) in tetrahydrofuran (6 mL) was treated with a 2N aqueous potassium hydroxide solution (6 mL) and was warmed to 80° C., where it stirred overnight. At this time, the reaction was concentrated in vacuo and was then carefully brought to pH ˜7 with a 2N aqueous hydrochloric acid solution. The material was then diluted with water (25 mL) and extracted with a 10% methanol/methylene chloride solution (2×25 mL). The combined organics were dried over magnesium sulfate, filtered and rinsed with methylene chloride, and concentrated in vacuo onto Celite®. Flash chromatography (40 g silica gel column, 1-50% ethyl acetate/hexanes) afforded 2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one as an off-white solid (53.7 mg, 16.9%). 1H NMR (300 MHz, DMSO-d6) δ ppm −0.08 (s, 9H) 0.82 (t, J=8.10 Hz, 2H) 3.50 (t, J=8.10 Hz, 2H) 5.42 (s, 2H) 6.53 (d, J=3.20 Hz, 1H) 7.26 (br. s., 1H) 12.98 (br. s., 1H). LC-MS calcd. for C12H19ClN3O2Si [(M+H)+] 300, obsd. 300.0.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe material was then diluted with water (25 mL)
  3. extractionextracted with a 10% methanol/methylene chloride solution (2×25 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. washrinsed with methylene chloride
  7. concentrationconcentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-ec3df30595bd4ea880a6f4da26641635
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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