N,N-Dimethylethylenediamine → HCID 59333652, compound

HRID 1876517Notes

Reaction equation

HRID 1876517 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]([CH2:31][CH:32]2[CH2:34][CH2:33]2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:13]=[C:12]([C:23]1[C:24]([CH3:30])=[N:25][C:26]([NH2:29])=[N:27][CH:28]=1)[N:11]=2>CS(C)=O>[NH2:29][C:26]1[N:25]=[C:24]([CH3:30])[C:23]([C:12]2[N:11]=[C:10]3[C:15]([N:16]=[C:8]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[N:9]3[CH2:31][CH:32]3[CH2:34][CH2:33]3)=[C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:13]=2)=[CH:28][N:27]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 593334985-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine

Product 1

HCID 59333652HCID 59333652, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

N,N-Dimethylethylenediamine (110 mg, 1.3 mmol) and dimethyl sulfoxide (700 μl) were added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine (100 mg, 0.26 mmol) and the resulting mixture was stirred at 150° C. for 3 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was concentrated, and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (64 mg, 52%) as a pale yellow solid.

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. concentrationthe organic layer was concentrated
  3. customthe residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

Sources & evidence

ORD record
ord-a2b6912be6ef41e2abac66de93d77cc0
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

Loading…