2,4-Diaminotoluene → N2,N4-bis(3-amino-4-methylphenyl)-2,4-pyrimidinediamine

HRID 76524

Reaction equation

Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[CH3:17])[NH2:13]>CO.O>[NH2:9][C:10]1[CH:11]=[C:12]([NH:13][C:2]2[N:7]=[C:6]([NH:13][C:12]3[CH:14]=[CH:15][C:16]([CH3:17])=[C:10]([NH2:9])[CH:11]=3)[CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:15][C:16]=1[CH3:17]

Participants

Conditions

Temperature: 70 °C

Procedure

2,4-Dichloropyrimidine (45 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 3-amino-4-methylaniline (146 mg, 1.2 mmol) was added and the mixture was refluxed for 20 hours (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and subjected to column chromatography on silica gel (CHCl3-Acetone, 2:1) to give N2,N4-bis(3-amino-4-methylphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.13 (s, 1H), 6.95 (d, 2H, J=7.5 Hz), 6.82 (d, 2H, J=1.8 Hz), 6.60 (dd, 2H, J=1.8, 7.5 Hz), 6.17 (s, 1H), 2.12 (s, 6H);

Workup

temperatureThe mixture was cooled to 22° C.
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-d4b2a08c3d564737937bcb220a24c7e0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835430B2

Linked notes

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