Diisopropylethylamine → 2-[(2R)-2,4-dimethyl-1-piperazinyl]-4-pyrimidinamine

HRID 1396906Notes

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.Br[C:19]1[C:28]2[C:23](=C[CH:25]=[C:26](OC)[N:27]=2)[N:22]=[CH:21]C=1N>CN(C)C=O>[CH3:19][C@@H:28]1[CH2:23][N:22]([CH3:21])[CH2:25][CH2:26][N:27]1[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 2-chloro-4-pyrimidinamine (300 mg, 2.316 mmol), Hunig's base (809 μl, 4.63 mmol) and (3R)-1,3-dimethylpiperazine (Ref.: WO2009061879 (A1)) (650 mg, 3.47 mmol) in N,N-dimethylformamide (DMF) (3 ml) was heated in a microwave reactor at 220° C. for 60 min. The reaction mixture was purified by RP-HPLC to yield 2-[(2R)-2,4-dimethyl-1-piperazinyl]-4-pyrimidinamine (88 mg, 0.425 mmol, 18% yield). MS (ES+) m/z 208.0 (MH+).

Workup

customThe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record: ord-179763b6275c4891a04f594baf82c33f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901119B2

Reaction notes

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