2-Chloro-5-fluoropyrimidin-4-amine → 4-Amino-2-[1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidylamino]-5-fluoropyrimidine

HRID 258309Notes

Reaction equation

HRID 258309 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.[NH2:24][C:25]1[C:30]([F:31])=[CH:29][N:28]=[C:27](Cl)[N:26]=1>>[NH2:24][C:25]1[C:30]([F:31])=[CH:29][N:28]=[C:27]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][C:9]34[CH2:23][CH:16]([C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=53)[C:15]3[C:10]4=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:4][CH2:3]2)[N:26]=1

Participants

3

Reactant 2

HCID 2543722-Chloro-5-fluoropyrimidin-4-amineHCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 541281134-Amino-2-[1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidylamino]-5-fluoropyrimidine

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 4-amino-2-chloro-5-fluoropyrimidine, the hydrochloride salt of the title compound was obtained as a white solid (8%), mp 250°-254° C.; MS(CI): 416 (M+H); NMR (300 MHz, DMSO-d6): 10.25(br s, 1H), 8.60(br m, 1H), 8.10(m, 1H), 7.39-7.32(m, 4H), 7.03-6.95(m, 4H), 4.46(s, 1H), 4.36(s, 2H), 4.18-3.80(br m, 1H), 3.60-3.38(m, 4H), 2.75(s, 2H), 2.14-1.96(m, 4H).

Sources & evidence

ORD record
ord-8e7e105b457140289085ea35fa9ba1df
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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