2-Chloro-4-(2-ethylanilino)pyrimidine → 2-{4-[3-(N,N-Dimethyl)amino-2-hydroxypropoxy]anilino}-4-(2-ethylanilino)pyrimidine

HRID 347744Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH3:16])[CH:5]=[CH:4][N:3]=1.Cl.[CH3:18][N:19]([CH2:21][CH:22]([OH:32])[CH2:23][O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)[CH3:20]>C(O)CCC.CO>[CH3:20][N:19]([CH2:21][CH:22]([OH:32])[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:15][CH3:16])[CH:5]=[CH:4][N:3]=2)=[CH:30][CH:31]=1)[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-4-(2-ethylanilino)pyrimidine (Reference Example A-5; 210 mg, 0.90 mmol) was dissolved in n-butanol (20 ml). To this solution was added a hot solution of 4-[3-(N,N-dimethyl)amino-2-hydroxypropoxy]aniline hydrochloride (Reference Example D-1; 229 mg, 0.81 mmol) in methanol (2 ml). The reaction mixture was heated at 100° C. for 18 hours, allowed to cool to ambient temperature and then evaporated onto silica (3 ml). The residue was purified by column chromatography eluting with 0–5% 2.0M methanolic ammonia solution in DCM to give the title product as a colourless solid (201 mg, 61%). NMR (300 MHz): 1.09 (t, 3H), 2.17 (s, 6H), 2.31 (m, 2H), 2.58 (q, 2H), 3.80 (m, 3H), 5.96 (d, 1H), 6.72 (d, 2H), 7.20 (m, 3H), 7.36 (d, 1H), 7.53 (d, 2H), 7.89 (d, 1H), 8.56 (s, 1H), 8.76 (s, 1H); m/z: (ES+) 408.3 (MH+)

Workup

temperatureto cool to ambient temperature
customevaporated onto silica (3 ml)
customThe residue was purified by column chromatography
washeluting with 0–5% 2.0M methanolic ammonia solution in DCM

Sources & evidence

ORD record: ord-68df96258cb54c26bf5ced76a133e545
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176212B2

Reaction notes

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