[2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]cyclopentylamine → HCID 58315449, compound

HRID 1483050Notes

Reaction equation

HRID 1483050 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>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[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 1

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

Product 1

HCID 58315449HCID 58315449, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

To a stirred solution of [2-chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-cyclopentyl-amine (7.50 g, 23.3 mmol) in THF (45 mL) is added IN TBAF in THF (100 mL, 116 mmol) at room temperature. The reaction mixture is heated under reflux overnight. After cooling the mixture is partitioned between H2O and dichloromethane. The phases are separated and the aqueous layer is extracted with dichloromethane (×2). The combined organic extracts are dried (MgSO4), filtered and concentrated. The residue is purified by SiO2 chromatography eluting with a gradient of 10% EtOAc/petrol to 30% EtOAc/petrol to give 2-chloro-7-cyclopentyl-6-diethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine, (5.68 g, 76%). MS (ESI) m/z 324.1 (M+H)+

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling the mixture
  4. customis partitioned between H2O and dichloromethane
  5. customThe phases are separated
  6. extractionthe aqueous layer is extracted with dichloromethane (×2)
  7. dry with materialThe combined organic extracts are dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by SiO2 chromatography
  11. washeluting with a gradient of 10% EtOAc/petrol to 30% EtOAc/petrol

Sources & evidence

ORD record
ord-343af5d6d90f490a863070d9f92a9c6a
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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