2-Morpholinoethylamine → HCID 59333524, compound

HRID 421328Notes

Reaction equation

HRID 421328 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:11]1[N:12]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:13]2[C:18]([N:19]=1)=[C:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[N:16]=[C:15]([C:26]1[C:27]([CH3:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=1)[N:14]=2>CS(C)=O>[NH2:32][C:29]1[N:28]=[C:27]([CH3:33])[C:26]([C:15]2[N:14]=[C:13]3[C:18]([N:19]=[C:11]([NH:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[N:12]3[CH2:34][CH:35]3[CH2:37][CH2:36]3)=[C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:16]=2)=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 59333498HCID 59333498, compound

Product 1

HCID 59333524HCID 59333524, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

2-Morpholin-4-yl-ethylamine (162 mg, 1.25 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, 0.25 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 (101 mg, 75%) 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-b74267da931e4ca3b0748cdbc6423dc7
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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