Cyanogen Bromide → Quinazolin-2-amine

HRID 481136

Reaction equation

HRID 481136 reaction equation
[CH:1]1[C:6]2[N:7]=[C:8]3[N:13]([CH2:14][C:5]=2[C:4](Cl)=[C:3](Cl)[CH:2]=1)CC(=O)[NH:9]3.O.Cl.C(N(CC1C(N)=CC=C(Cl)C=1Cl)CC(O)=O)C.N#CBr>>[NH:9]=[C:8]1[N:13]=[CH:14][C:5]2[C:6](=[CH:1][CH:2]=[CH:3][CH:4]=2)[NH:7]1

Participants

5

Reactant 4

HCID 10476Cyanogen Bromide2×HCID 21885828Hydrate;hydrochloride2×HCID 67080112ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine2×HCID 135409400Anagrelide

Product 1

HCID 178508286Quinazolin-2-amine

Procedure

Commercially, as discussed in U.S. Pat. No. 5,801,245 and as shown in FIG. 1, Anagrelide has been prepared as the hydrochloride monohydrate (compound IV) from the intermediate, ethyl N-(6-amino-2,3-dichlorobenzyl)glycine (compound I) by reaction with cyanogen bromide in hot alcohol solution, or, preferentially, by reaction with cyanogen bromide in an aprotic solvent to give the iminoquinazoline intermediate (compound II) which is isolated and then reacted with a base in a hot solution of alcohol to form Anagrelide base (compound III).

Sources & evidence

ORD record
ord-cfab49f40e6e4e44a0f2973c0270664c
Source dataset
uspto-grants-2003_11
Patent number
US06653500B2

Linked notes

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