6-(5-Methyl-2-Furyl)-5-Nitropyrimidine-2,4-Diamine → 6-(5-Methyl-2-furyl)pyrimidine-2,4,5-triamine

HRID 750503Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[N:12]=[C:11]([NH2:13])[N:10]=[C:9]([NH2:14])[C:8]=2[N+:15]([O-])=O)=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[N:12]=[C:11]([NH2:13])[N:10]=[C:9]([NH2:14])[C:8]=2[NH2:15])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 6-(5-methyl-2-furyl)-5-nitropyrimidine-2,4-diamine (6.6 g, 29.6 mmol) and 10% Pd/C (0.66 g) in MeOH (100 mL) was heated at 40° C. under an atmosphere of H2 for 3 h, cooled to room temperature, filtered through Celite, and concentrated in vacuo to give the title compound (5.8 g, 99%) as an off-whited solid; IR νmax (DR)/cm−1 3333, 2237, 1634, 1458, 1237, 1025, 963 and 828; NMR δH (400 MHz, DMSO) 6.77 (1H, dd, J 0.5, 3.2 Hz), 6.21-6.17 (3H, m), 5.14 (2H, s), 4.21 (2H, s), and 2.35 (3H, s).

Workup

temperaturecooled to room temperature
filtrationfiltered through Celite
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3dd5da3f832a4f20b4a690be90bbacff
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405219B2

Reaction notes

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