2-Amino-4,6-dichloropyrimidine → 6-Chloro-N4-(1,1-dimethyl-2-phenylethyl)-2,4-pyrimidinediamine

HRID 2367260Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2-methyl-1-phenyl-2-propanamine hydrochloride (742 mg, 4 mmol), 4,6-dichloro-2-pyrimidinamine (438 mg, 2.67 mmol) and Hunig's base (1.55 g, 12 mmol) in CH3CN (8 mL) was stirred and heated for 6 hours at 160° C. in a Biotage Initiator microwave synthesizer. The mixture was cooled to room temperature and concentrated to dryness. The resulting solids were partitioned between EtOAc and water, and the organic layer was dried over Na2SO4, filtered and concentrated to dryness. Purification by reverse phase chromatography using CH3CN in water from 45% to 65% (0.08% ammonium hydrogen carbonate) in 18 min, afforded the title compound (373 mg) as a white solid. LC-MS (ES) m/z=277.0 [M+H]+.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated to dryness
customThe resulting solids were partitioned between EtOAc and water
dry with materialthe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
customPurification by reverse phase chromatography
customin 18 min

Sources & evidence

ORD record: ord-4c89eb78c272415e85a7dc478c89c68c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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