2-Chloroaniline → 6-chloro-N4-(2-chlorophenyl)pyrimidine-4,5-diamine

HRID 1098222Notes

Reaction equation

Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13]>C(O)CO>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[Cl:10])[C:7]=1[NH2:8]

Participants

Conditions

Temperature: 100 °C

Procedure

4,6-Dichloropyrimidin-5-amine (CAS no. 5413-85-4) (2 g, 12.20 mmol) and 2-chloroaniline (CAS no. 95-51-2) (1.556 g, 12.20 mmol) were dissolved in ethylene glycol (12 mL) and sealed into a microwave tube. The reaction was heated to 100° C. for 1 hour in the microwave reactor and cooled to room temperature. The reaction mixture was quenched with water (50 mL), extracted with EtOAc (3×50 mL), the organic layer was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, eluting with 0 to 60% EtOAc in isohexane to afford the product (2.65 g, 85%). 1H NMR (400 MHz, DMSO) 65.38 (s, 2H), 7.19-7.25 (m, 1H), 7.32-7.38 (m, 1H), 7.49-7.54 (m, 1H), 7.57-7.62 (m, 1H), 7.73 (s, 2H), 7.19-7.25 (s, 1H); m/z (ES+), (M+H)+=255.25; HPLC tR=1.82 min.

Workup

customsealed into a microwave tube
temperaturecooled to room temperature
customThe reaction mixture was quenched with water (50 mL)
extractionextracted with EtOAc (3×50 mL)
dry with materialthe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated
customto afford crude product
customThe crude product was purified by flash silica chromatography
washeluting with 0 to 60% EtOAc in isohexane

Sources & evidence

ORD record: ord-c7cb725c583b4a5e98958a2305edac38
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143263B2

Reaction notes

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