2-Bromopyrimidine → N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-amine
Reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2[C@@H](OCC)CN(C3SC=CN=3)C2)=NC=1CC.Br[C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1.[CH2:40]([O:42][C@H:43]1[CH2:47][NH:46][CH2:45][C@H:44]1[NH:48][C:49]1[C:54]([CH2:55][CH3:56])=[N:53][C:52]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][C:58]=2[CH3:65])=[C:51]([CH2:66][CH3:67])[N:50]=1)[CH3:41]>>[CH2:40]([O:42][C@H:43]1[CH2:47][N:46]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:45][C@H:44]1[NH:48][C:49]1[C:54]([CH2:55][CH3:56])=[N:53][C:52]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][C:58]=2[CH3:65])=[C:51]([CH2:66][CH3:67])[N:50]=1)[CH3:41]Participants
4
Reactant 3
Product 1
Procedure
Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl}-3,6-diethylpyrazin-2-amine but substituting 2-bromopyrimidine and starting with N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.15, 1.28, 2.13, 2.48, 2.74, 3.51, 3.77, 3.85, 3.98, 4.25, 4.90, 5.20, 6.56, 6.81, 7.12, 8.37; IR (diffuse reflectance) 2970, 2402 (w), 2350 (w), 2307 (w), 2212 (w), 2169 (w), 1583 (s), 1568, 1548 (s), 1508 (s), 1475 (s), 1393, 1383, 1242, 798 cm−1 HRMS (ESI) calcd for C26H34N6O2+H1 463.2821. found 463.2816.
Sources & evidence
- ORD record
- ord-5f843654b3d74d65826f09dd48471b88
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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