2-Bromopyrimidine → 5-(2,6-dimethoxypyridin-3-yl)-N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine
Reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:8][N:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:6][C@H:5]1[NH:15][C:16]1[C:21]([CH2:22][CH3:23])=[N:20][C:19]([C:24]2[C:25](C)=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[C:18]([CH2:33][CH3:34])[N:17]=1)[CH3:2].BrC1N=CC=CN=1.[CH3:42][O:43]C1C(C2N=C(CC)C(N[C@H]3[C@@H](OCC)CNC3)=NC=2CC)=CC=C(OC)N=1>>[CH3:42][O:43][C:25]1[C:24]([C:19]2[N:20]=[C:21]([CH2:22][CH3:23])[C:16]([NH:15][C@H:5]3[C@@H:4]([O:3][CH2:1][CH3:2])[CH2:8][N:7]([C:9]4[N:10]=[CH:11][CH:12]=[CH:13][N:14]=4)[CH2:6]3)=[N:17][C:18]=2[CH2:33][CH3:34])=[CH:29][CH:28]=[C:27]([O:30][CH3:31])[N:26]=1Participants
4
Reactant 3
Product 1
Procedure
Following the procedure for the preparation of N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine but substituting 2-bromopyrimidine and starting with 5-(2,6-dimethoxypyridin-3-yl)-N-[(3R,4S)4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (400 MHz, CDCl3) δ) 8.35, 7.53, 6.52, 6.42, 5.18, 4.90, 4.20, 3.97, 3.93, 3.89, 3.77, 3.52, 2.72, 2.52, 1.33–1.25, 1.18; IR (diffuse reflectance) 2402 (w), 2347 (w), 2307 (w), 2264 (w), 2194 (w), 1601, 1582 (s), 1566, 1547 (s), 1510 (s), 1474 (s), 1395, 1377 (s), 1312 (s), 1022 cm−1 HRMS (ESI) calcd for C25H33N7O3+H1 480.2723. found 480.2715.
Sources & evidence
- ORD record
- ord-683bb6c17e5a4aacb0df95cc71e62a01
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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