2-Acetylfuran → 5-Bromo-4-(2-furyl)-2-pyrimidinylamine

HRID 1355828Notes

Reaction equation

HRID 1355828 reaction equation
[C:1]([C:4]1O[CH:6]=[CH:7][CH:8]=1)(=O)[CH3:2].COC(OC)N(C)C.[C:17](=[O:20])(O)O.[NH2:21][C:22]([NH2:24])=[NH:23].C[O-].[Na+].[Br:28]N1C(=O)CCC1=O>CN(C=O)C.CO.C(O)(=O)C>[Br:28][C:1]1[C:4]([C:8]2[O:20][CH:17]=[CH:6][CH:7]=2)=[N:23][C:22]([NH2:24])=[N:21][CH:2]=1

Participants

9

Reactant 5

HCID 145052-AcetylfuranHCID 67184N-bromobutanimideHCID 78373Dimethylformamide dimethyl acetalHCID 286947Carbonic acid-guanidine (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 185072635-Bromo-4-(2-furyl)-2-pyrimidinylamine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

From 2-acetylfuran and N,N-dimethylformamide dimethyl acetal in DMF. Then treatment with guanidine carbonate and sodium methylate in methanol. Then treatment with N-bromosuccinimide in acetic acid. EI-MS m/e (%): 241 (M{81Br}+, 98), 239 (M{81Br}+, 100).

Sources & evidence

ORD record
ord-68d521d2a63a4b7e87ca2322655afbeb
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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