Diisopropylethylamine → 4-Chloro-2-(cyclopropylmethyl-amino)-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

HRID 1838176Notes

Reaction equation

HRID 1838176 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.N[C:19]1([CH3:22])C[CH2:20]1.[CH2:23]([N:25](C(C)C)C(C)C)C>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4]([NH:25][CH2:23][CH:22]2[CH2:19][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 116511491-MethylcyclopropanamineHCID 187532814-Chloro-6-(2-hydroxy-ethylamino)-2-methanesulfonyl-pyrimidine-5-carbonitrile

Product 1

HCID 187532604-Chloro-2-(cyclopropylmethyl-amino)-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described in example 47a, the crude 4-chloro-6-(2-hydroxy-ethylamino)-2-methanesulfonyl-pyrimidine-5-carbonitrile was treated with amino-methyl-cyclopropane in dioxane in the presence of N-ethyl-diisopropylamine at 40° C. to yield 4-chloro-2-(cyclopropylmethyl-amino)-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=268.

Sources & evidence

ORD record
ord-b23fbded299947afbcc2a53865649dc8
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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