2,4-Diamino-5-(1,2,3,4-tetrahydro-8-methoxy-6-quinolylmethyl)pyrimidine → 5-[(8-Methoxyquinolin-6-yl)methyl]pyrimidine-2,4-diamine

HRID 279979Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([O:20][CH3:21])[CH:19]=2)[NH:16][CH2:15][CH2:14][CH2:13]3)=[CH:4][N:3]=1>[Pd].C1(C(C)C)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([O:20][CH3:21])[CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

The product of Example 2 was oxidised using 20% palladium on charcoal in 50 ml of cumene, by heating at 150° C. for 21 hours. After the catalyst was removed and the solvent evaporated, the residue was purified on a silica gel column which was eluted with methylene chloride:methanol/19:1. This produced 0.51 g (35%) of the title compound, which melted at 285°-287° after recrystallisation from betamethoxyethanol. Anal. Calcd. for C15H15N5O: C, 64.04; H, 5.37; N, 24.89. Found: C, 63.88; H, 5.37; N, 24.84.

Workup

customAfter the catalyst was removed
customthe solvent evaporated
customthe residue was purified on a silica gel column which
washwas eluted with methylene chloride
customThis produced 0.51 g (35%) of the title compound, which melted at 285°-287° after recrystallisation from betamethoxyethanol

Sources & evidence

ORD record: ord-1992c08263a54b7e8082bb60778c5538
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587341

Reaction notes

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