4-(2-Chloroethyl)morpholine → [4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-[3-(2-morpholin-4-yl-ethoxymethyl)-phenyl]-amine

HRID 599169Notes

Reaction equation

HRID 599169 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CC#N>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 22744124{3-[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-methanol

Product 1

HCID 10002542[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-[3-(2-morpholin-4-yl-ethoxymethyl)-phenyl]-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By alkylation of {3-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-methanol with 4-(2-chloro-ethyl)-morpholine. Yellow solid. Anal. RP-HPLC: tR=8.5 min (10-70% MeCN, purity >95%). 1H-NMR (DMSO-D6) δ: 2.56 (s, 3H, CH3), 2.57 (s, 3H, CH3), 2.63 (m, 2H, CH2), 3.58 (m, 4H, J=4.5 Hz, CH2×2), 4.14 (t, 2H, J=7.5 Hz, CH2), 4.58 (d, 2H, J=5.0 Hz, CH2), 5.28 (t, 1H, J=5.5 Hz, NH), 7.06 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.26 (m, 2H, Ph-H), 7.36 (s, 1H, Ph-H), 7.42 (m, 1H, Ph-H), 8.43 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 9.12 (sbr, 1H, Ph-H). MS (ESI+) m/z 426.46 [M+H]+ (C22H27N5O2S requires 425.55).

Sources & evidence

ORD record
ord-e652dc51c01a4c9ab8f3795aaf2e9f38
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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