Triethylamine → 4-Chloro-6-[(2R)-2-ethyl-1-pyrrolidinyl]-2-pyrimidinamine

HRID 2367225Notes

Reaction equation

HRID 2367225 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1)[CH3:2].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([NH2:16])[N:10]=1.CCN(CC)CC>CC#N>[Cl:8][C:9]1[CH:14]=[C:13]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[CH2:1][CH3:2])[N:12]=[C:11]([NH2:16])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidineHCID 10931375(R)-2-ethylpyrrolidine

Product 1

HCID 585046974-Chloro-6-[(2R)-2-ethyl-1-pyrrolidinyl]-2-pyrimidinamineYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2R)-2-ethylpyrrolidine (80 mg, 0.59 mmol), 4,6-dichloro-2-pyrimidinamine (119 mg, 0.726 mmol) and Et3N (0.25 mL, 1.77 mmol) in CH3CN (6 mL) was stirred overnight at 80° C. The mixture was poured onto water (˜150 mL), sonicated and filtered to afford the title compound (94 mg, 70%) as a white solid. LC-MS (ES) m/z=227, 229 [M+H]+.

Workup

  1. additionThe mixture was poured onto water (˜150 mL)
  2. customsonicated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4a413a2b93614d3998a307335c9fe5c9
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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