Tetrabutylammonium Fluoride → HCID 58315449, compound

HRID 2359567Notes

Reaction equation

HRID 2359567 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]([C:14]#[C:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[CH:4][N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:14]=[C:15]([CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[N:8]([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58315397[2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]cyclopentylamine

Product 1

HCID 58315449HCID 58315449, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of [2-chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-cyclopentyl amine (5.21 g, 16 mmol) in THF is added 1M tetra-n-butylammonium floride in THF (TBAF) (97 mL, 97 mmol) and heated to 65° C. for 2 hour. Solvent is removed and column is run using heptane/ethyl acetate from 5% to 15% to give 2-chloro-7-cyclopentyl-6-diethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine (4.26 g, 82%). MS (ESI) m/z 324.5 (M+H)+

Workup

  1. customSolvent is removed

Sources & evidence

ORD record
ord-bdd18fa9ff6a4cf88b70d24dd632dda4
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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