2-(Dimethylamino)ethanol → 2-(2-chloropyrimidin-5-yloxy)-N,N-dimethylethanamine

Reaction equation

NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(O)=CC=2)C=1C#N.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][OH:27].[Cl:29][C:30]1[N:35]=[CH:34][C:33](O)=[CH:32][N:31]=1>>[Cl:29][C:30]1[N:35]=[CH:34][C:33]([O:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])=[CH:32][N:31]=1

Participants

Reactant 3

HCID 79022-(Dimethylamino)ethanol

HCID 145957002-Chloro-5-pyrimidinol

HCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 594474952-(2-chloropyrimidin-5-yloxy)-N,N-dimethylethanamine

Procedure

Compound 112B was prepared in a similar manner to the synthesis of step 1 of Example 35 by substituting compound 34D and compound 31F with 2-(dimethylamino)ethanol and compound 112A, respectively: ESI (+)MS: 201 (M+H)−.

Sources & evidence

ORD record: ord-a1eb909c926f4edcaf8e0c36d7162c66
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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