4,6-Dichloro-n-methylpyrimidin-2-amine → 4-Chloro-6-[(2R)-2-ethyl-1-pyrrolidinyl]-N-methyl-2-pyrimidinamine

HRID 2367631Notes

Reaction equation

[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1)[CH3:2].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([NH:16][CH3:17])[N:10]=1>O1CCOCC1.C([O-])(O)=O.[Na+]>[Cl:8][C:9]1[CH:14]=[C:13]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[CH2:1][CH3:2])[N:12]=[C:11]([NH:16][CH3:17])[N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2R)-2-ethylpyrrolidine (0.8 g, 5.90 mmol) and 4,6-dichloro-N-methyl-2-pyrimidinamine (0.997 g, 5.60 mmol) in 1,4-dioxane (40 mL) and saturated aqueous NaHCO3 (20 mL) was stirred overnight at 100° C. into a sealed tube. The reaction mixture was poured onto water (˜400 mL). A white precipitate was formed. The aqueous mixture was filtered, and the white solid was washed with water (˜100 mL). The wet solid was dried overnight on vacuum at 40° C. to afford the title compound (1.19 g). LC-MS (ES) m/z=241 [M+H]+.

Workup

additionThe reaction mixture was poured onto water (˜400 mL)
customA white precipitate was formed
filtrationThe aqueous mixture was filtered
washthe white solid was washed with water (˜100 mL)
customThe wet solid was dried overnight on vacuum at 40° C.

Sources & evidence

ORD record: ord-0ce5a86eeaa9494f8732a6a98ddb3471
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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