2,4,5-Trichloropyrimidine → HCID 131729551, compound

HRID 1687120Notes

Reaction equation

HRID 1687120 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[C:14]1[N:19]=[C:18](Cl)[C:17]([Cl:21])=[CH:16][N:15]=1.[CH3:22][O:23][CH2:24][CH2:25][N:26]1[CH2:32][CH2:31][C:30]2[CH:33]=[C:34]([NH2:37])[CH:35]=[CH:36][C:29]=2[CH2:28][CH2:27]1>>[Cl:21][C:17]1[C:16]([NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:15][C:14]([NH:37][C:34]2[CH:35]=[CH:36][C:29]3[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][O:23][CH3:22])[CH2:32][CH2:31][C:30]=3[CH:33]=2)=[N:19][CH:18]=1

Participants

4

Reactant 3

HCID 2372592,4,5-TrichloropyrimidineHCID 27797102-(1H-pyrazol-1-yl)anilineHCID 574160893-(2-Methoxyethyl)-2,3,4,5-tetrahydro-1h-3-benzazepin-7-amine

Product 1

HCID 131729551HCID 131729551, compound

Procedure

5-Chloro-N*2*-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-N*4*-(2-pyrazol-1-yl-phenyl)-pyrimidine-2,4-diamine was prepared from 2-(1H-pyrazol-1-yl)aniline, 2,4,5-trichloropyrimidine, and 3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine in an analogous manner to Example 308. Product isolated as a white foam (108 mg, 65%). LCMS (m/e) 490 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 10.20 (s, 1H), 8.52 (d, 1H, J=8.3 Hz), 8.04 (d, 1H, J=1.6 Hz), 7.86 (s 1H), 7.81 (d, 1H, J=1.9 Hz), 7.41-7.14 (m, 5H), 7.10-6.90 (m, 2H), 6.54-6.50 (m, 1H), 3.69-3.54 (m, 2H), 3.39 (s, 3H), 2.96-2.86 (m, 4H), 2.80-2.69 (m, 6H).

Sources & evidence

ORD record
ord-2eae76dc31764cd39341f8bcbe46a142
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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