Formaldehyde → [2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2-ethyl-4-methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

HRID 14905Notes

Reaction equation

HRID 14905 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]4[CH2:31][CH3:32])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:33]=O>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]4[CH2:30][CH2:29][N:28]([CH3:33])[CH2:27][CH:26]4[CH2:31][CH3:32])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 58603775[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S)-ethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

Product 1

HCID 58603732[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2-ethyl-4-methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

Procedure

Compound 193 was coupled with formaldehyde following procedure E. LC-MS showed the product had the expected M+H+ of 452. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.68 (s, 1H), 8.36 (d, 2H), 7.92 (d, 1H), 7.67 (m, 2H), 6.99 (d, 2H), 6.72 (s, 1H), 5.07 (d, 1H), 4.36 (s, 1H), 3.43 (m, 7H), 3.04 (m, 4H), 2.36 (s, 1H), 2.05 (m, 1H), 2.00 (s, 3H), 1.15 (t, 3H).

Sources & evidence

ORD record
ord-7fd4adc237164b1ab26830572bb60ad4
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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