Hydrochloric Acid → 2-Chloro-5-iodo-4-(pyrrolidin-1-yl)pyrimidine

HRID 2284748Notes

Reaction equation

HRID 2284748 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([I:9])=[CH:4][N:3]=1.Cl.C([N:14]([CH2:18][CH3:19])[CH:15]([CH3:17])C)(C)C>O1CCCC1.N1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:14]2[CH2:15][CH2:17][CH2:19][CH2:18]2)[C:5]([I:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2634382,4-Dichloro-5-iodopyrimidine

Product 1

HCID 900517752-Chloro-5-iodo-4-(pyrrolidin-1-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31268PyrrolidineSolvent

Procedure

To a solution of 2,4-dichloro-5-iodopyrimidine (5.00 g) synthesized according to the method described in WO2008/155140 A1 in tetrahydrofuran (50 mL), N,N-diisopropylethylamine (3.49 mL) and pyrrolidine (1.65 mL) were added under ice cooling, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, 1.0 mol/L aqueous hydrochloric acid was added. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 2-chloro-5-iodo-4-(pyrrolidin-1-yl)pyrimidine (H1, 4.49 g).

Workup

  1. additionwere added under ice cooling
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b50ef418ea04228b9ba0b1f944cb14c
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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