2-Chloro-5-phenylpyrimidine → 2-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidylamino]-5-phenylpyrimidine

HRID 258311Notes

Reaction equation

HRID 258311 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]23[CH2:23][CH:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=42)[C:15]2[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.Cl[C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][N:26]=1>>[CH:21]1[C:22]2[C:9]3([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:25]5[N:26]=[CH:27][C:28]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=6)=[CH:29][N:30]=5)[CH2:3][CH2:4]4)[CH2:23][CH:16]([C:15]4[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 6053202-Chloro-5-phenylpyrimidineHCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 217558602-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidylamino]-5-phenylpyrimidine

Procedure

Using a procedure similar to that described in Example 86 except starting with 4-amino-1-(9,10-dihydro-9,10-methanoanthracene-9-ylmethyl)piperidine (prepared as described in Example 8b) and 2-chloro-5-phenylpyrimidine the hydochloride salt of the title compound was obtained as a white solid (60%), mp 292°-294° C.; MS(CI): 459 (M+H); NMR (300 MHz, DMSO-d6): 9.95(br s, 1H), 8.70-8.66(m, 2H), 7.66-7.62(m, 3H), 7.47-7.33(m, 7H), 7.04-6.96(m, 4H), 4.46(s, 1H), 4.35-4.33(m, 2H), 4.25-4.00(br m, 1H), 3.60-3.35(m, 4H), 2.74(s, 2H), 2.15-1.91(m, 4H).

Sources & evidence

ORD record
ord-564cee93b59b4f3e85b30560e97649df
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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