Guanidine Hydrochloride → 5-[(4,8-Dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine

HRID 279992Notes

Reaction equation

HRID 279992 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:25][CH3:26])[CH:9]=[C:10]([CH2:13][C:14](=[CH:17]NC3C=CC=CC=3)[C:15]#[N:16])[CH:11]=2)[N:6]=[C:5]([CH3:27])[CH:4]=1.N(C(C)C#N)C1C=CC=CC=1.C[O-].[Na+].Cl.[NH2:43][C:44]([NH2:46])=[NH:45]>CS(C)=O.C(O)C>[NH2:45][C:44]1[N:46]=[C:15]([NH2:16])[C:14]([CH2:13][C:10]2[CH:11]=[C:12]3[C:7](=[C:8]([O:25][CH3:26])[CH:9]=2)[N:6]=[C:5]([CH3:27])[CH:4]=[C:3]3[O:2][CH3:1])=[CH:17][N:43]=1

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium Methoxide2×HCID 155768252-(Phenylamino)propanenitrileHCID 67937090HCID 67937090, compound

Product 1

HCID 145703385-[(4,8-Dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The aldehyde from above was converted to 2-(4,8dimethoxy-2-methyl-6-quinolylmethyl)-3-anilinoacrylonitrile with anilinopropionitrile and sodium methylate in dimethyl sulfoxide on a 1.4 mmol scale in the same manner as in Example 5-A. The crude product from this reaction was condensed with guanidine hydrochloride and sodium methylate in ethanol as in Example 5-B to give the crude product.

Sources & evidence

ORD record
ord-151bb5f14ab9486c814ab0388aad64d4
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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