Diisopropylethylamine → HCID 68288030, compound

HRID 1396909Notes

Reaction equation

HRID 1396909 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][N:19]([CH3:25])[C@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1>CN(C)C=O>[CH3:18][N:19]([CH3:25])[C@H:20]1[CH2:24][CH2:23][N:22]([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=2)[CH2:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3457522-Chloro-4-aminopyrimidineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidine

Product 1

HCID 68288030HCID 68288030, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 2-chloro-4-pyrimidinamine (200 mg, 1.544 mmol), Hunig's base (539 μl, 3.09 mmol) and (3S)—N,N-dimethyl-3-pyrrolidinamine (294 μl, 2.316 mmol) in N,N-dimethylformamide (DMF) (2 ml) was heated to 220° C. via a microwave reactor for 30 min. The reaction mixture was purified by RP-HPLC to yield 2-[(3S)-3-(dimethylamino)-1-pyrrolidinyl]-4-pyrimidinamine (205 mg, 0.989 mmol, 64% yield). MS (ES+) m/z 208.0 (MH+).

Workup

  1. customThe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-158dd5f833224258a4a06c03d27f9e4d
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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