2-Bromopyrimidine → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl 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.[Cl:40][C:41]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[CH:43][C:42]=1[C:49]1[N:50]=[C:51]([CH2:66][CH3:67])[C:52]([NH:57][C@H:58]2[C@@H:62]([O:63][CH2:64][CH3:65])[CH2:61][NH:60][CH2:59]2)=[N:53][C:54]=1[CH2:55][CH3:56]>>[Cl:40][C:41]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[CH:43][C:42]=1[C:49]1[N:50]=[C:51]([CH2:66][CH3:67])[C:52]([NH:57][C@H:58]2[C@@H:62]([O:63][CH2:64][CH3:65])[CH2:61][N:60]([C:34]3[N:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[CH2:59]2)=[N:53][C:54]=1[CH2:55][CH3:56]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 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.17, 1.26–1.34, 2.51, 2.76, 3.54, 3.78, 3.86, 3.97, 4.27, 4.91, 5.25, 6.61, 6.90, 7.02, 7.25, 8.40; IR (diffuse reflectance) 2971, 2392 (w), 2352 (w), 2307 (w), 2265 (w), 2170 (w), 1583 (s), 1569, 1549 (s), 1508 (s), 1481 (s), 1475 (s), 1397, 1392, 1384 cm−1 HRMS (EI) calcd for C25H31ClN6O2 482.2197. found 482.2192.
Sources & evidence
- ORD record
- ord-bba5a6f81af94fefb45cf0348bbcca24
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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