Diisopropylethylamine → 2-(4-Methyl-4,7-diazaspiro[2.5]oct-7-yl)-4-pyrimidinamine

HRID 1396922Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[CH3:9]CN(C(C)C)C(C)C.BrC1[C:28]2[C:23](=[CH:24][CH:25]=[C:26](OC)[N:27]=2)[N:22]=[CH:21]C=1N>CN(C)C=O>[CH3:9][N:22]1[CH2:21][CH2:26][N:27]([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=2)[CH2:28][C:23]21[CH2:24][CH2:25]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chloro-4-pyrimidinamine (200 mg, 1.544 mmol), Hunig's base (1348 μl, 7.72 mmol) and 4-methyl-4,7-diazaspiro[2.5]octane (Ref.: WO2009061879 (A1)) (338 mg, 1.698 mmol) in N,N-dimethylformamide (DMF) (1.7 ml) was heated to 120° C. via a microwave reactor for 15 min. The reaction mixture was purified by RP-HPLC to yield 2-(4-methyl-4,7-diazaspiro[2.5]oct-7-yl)-4-pyrimidinamine (113 mg, 0.515 mmol, 33% yield). MS (ES+) m/z 220.1 (MH+).

Workup

customThe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record: ord-b9703b7410944f578ab061f3b73c8791
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901119B2

Reaction notes

Loading…