2-Amino-4,6-dichloropyrimidine → HCID 58504602, compound

HRID 2367283Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH2:10]([C@@H:12]1[CH2:17][O:16][CH2:15][CH2:14][NH:13]1)[CH3:11].CCN(C(C)C)C(C)C>CC#N>[Cl:8][C:6]1[CH:7]=[C:2]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][C@H:12]2[CH2:10][CH3:11])[N:3]=[C:4]([NH2:9])[N:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To 4,6-dichloro-2-pyrimidinamine (240 mg, 1.46 mmol) in CH3CN (8 mL) were added (3R)-3-ethylmorpholine (244 mg, 1.61 mmol) and Hunig's base (1.02 mL, 5.85 mmol), and the reaction mixture was heated in a microwave at 150° C. for a total of 3 hours, checking the progression of the reaction at regular intervals. The mixture was evaporated under vacuum, and the resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×) and CH2Cl2 (2×). The organics were washed with water and brine, dried (MgSO4), filtered and evaporated. The resulting material was triturated with Et2O and dried in vacuo to afford the title compound (307 mg). LC-MS (ES) m/z=243, 245 [M+H]+.

Workup

customthe progression of the reaction at regular intervals
customThe mixture was evaporated under vacuum
customthe resulting residue was partitioned between EtOAc and water
extractionThe aqueous layer was extracted with EtOAc (2×) and CH2Cl2 (2×)
washThe organics were washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customThe resulting material was triturated with Et2O
customdried in vacuo

Sources & evidence

ORD record: ord-ef93fe14888749f2b221a66b05d35c3e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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