2-Morpholinoethanol → 4-[5-Bromo-2-(2-morpholin-4-yl-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamine

HRID 28641

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18]C)=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH2:15])[N:9]=2)[CH:7]=1.NC1N=C(C2C=C(Br)C=CC=2O)C=C(Cl)N=1.[N:36]1(CCO)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH2:15])[N:9]=2)[CH:7]=1

Participants

Reactant 3

HCID 611632-Morpholinoethanol

HCID 860043744-(5-Bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine

HCID 1360800122-(2-Amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol

Product 1

HCID 865946044-[5-Bromo-2-(2-morpholin-4-yl-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamineYield 41%

Procedure

Following the method described in Example 135 for the synthesis of 4-(5-bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine, 2-(2-amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol and 2-morpholin-4-yl-ethanol provided 4-[5-bromo-2-(2-morpholin-4-yl-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamine (41% yield).

Sources & evidence

ORD record: ord-6c7f968354a6410e83123b30300d2874
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Linked notes

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