Phenol, 4-(2-aminoethyl)-2-methyl- → 2-Methyl-4-(2-{4-[3-(2(S)-methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 2386480Notes

Reaction equation

HRID 2386480 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[C@@H:10]([CH3:28])[CH2:9]1)=O)(C)(C)C.[NH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([CH3:39])[CH:33]=1>>[CH3:39][C:34]1[CH:33]=[C:32]([CH2:31][CH2:30][NH:29][C:23]2[N:22]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:11]4[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]4[CH3:28])[CH:16]=3)[CH:26]=[CH:25][N:24]=2)[CH:37]=[CH:36][C:35]=1[OH:38]

Participants

3

Reactant 2

HCID 11286912Phenol, 4-(2-aminoethyl)-2-methyl-HCID 866032844-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3-(S)-methyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586036822-Methyl-4-(2-{4-[3-(2(S)-methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 68 was coupled with 4-(2-amino-ethyl)-2-methyl-phenol following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 418. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.32 (s, 1H), 8.26 (d, 1H), 7.78 (d, 1H), 7.64 (t, 1H), 7.45 (d, 1H), 7.13 (d, 1H), 6.98 (s, 1H), 6.88 (d, 1H), 6.60 (d, 1H), 4.71 (d, 1H), 3.99 (d, 1H), 3.84 (s, 2H), 3.45 (m, 3H), 3.23 (m, 3H), 3.02 (t, 1H), 2.86 (t, 2H), 2.07 (s, 3H), 1.54 (d, 3H).

Sources & evidence

ORD record
ord-bbeba00463ee437e8e6b5be2613c318e
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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