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

HRID 2209604Notes

Reaction equation

HRID 2209604 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]([I:31])=[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:30]=[CH:29][C:28]([I:31])=[CH:27][N:26]=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 17142232-Chloro-5-iodopyrimidineHCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 539970372-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidylamino]-5-iodopyrimidine

Procedure

Using a procedure similar to that described in Example 86 except starting with 4-amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine (prepared as described in Example 8b) and 2-chloro-5-iodopyrimidine, the title compound was obtained as a white solid (100%), mp 240° C. (dec); MS(CI): 509 (M+H); NMR (300MHz, DMSO-d6): 9.95(br s, 1H), 8.50-8.45(m, 2H), 7.68(b, 1H), 7.37-7.32(m, 4H), 7.03-6.95(m, 4H), 4.45(s, 1H), 4.35-4.31(m, 2H), 4.18-3.80(br m, 1H), 3.58-3.38(m, 4H), 2.73(s, 2H), 2.08-1.87(m, 4H).

Sources & evidence

ORD record
ord-950b5ae3be764858aad45fde9cb5e74e
Source dataset
uspto-grants-1995_10
Patent number
US05455246

Reaction notes

Loading…