Guanidine Hydrochloride → 4-(4-bromophenyl)pyrimidin-2-amine

HRID 1891096Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=O.[CH3:11]OC(OC)N(C)C.Cl.[NH2:20][C:21]([NH2:23])=[NH:22].C(=O)([O-])[O-].[K+].[K+].C(OCCO)C>>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2[CH:1]=[CH:11][N:20]=[C:21]([NH2:23])[N:22]=2)=[CH:5][CH:6]=1

Participants

Reactant 5

HCID 5742Guanidine Hydrochloride

HCID 7466p-Bromoacetophenone

HCID 8076Glycol monoethyl ether

HCID 11430Potassium Carbonate

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 45901504-(4-bromophenyl)pyrimidin-2-amine

Procedure

4-(4-Bromophenyl)pyrimidin-2-amine was prepared by the reaction of 4-bromoacetophenone with N,N-dimethylformamide dimethyl acetal followed by cyclisation with guanidine hydrochloride in presence of suitable base such as potassium carbonate in refluxing dimethylene glycol monoethyl ether. 1H NMR (300 MHz, DMSO-d6) 6 6.69 (br s, 2H), 7.11 (d, J =5.1 Hz, 1H), 7.67 (d, J =8.4 Hz, 2H), 7.99 (d, J =8.1 Hz, 2H), 8.29 (d, J =4.8, 1H.

Sources & evidence

ORD record: ord-56907db823ec4a80a25ec7376c2254d8
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507503B2

Reaction notes

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