Triethylamine → HCID 9865523, compound

HRID 1280558Notes

Reaction equation

HRID 1280558 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH3:26])[C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[CH2:17][C:11]3=[CH:10][N:9]=2)[CH2:3][CH2:2]1.Br[CH2:28][CH2:29][OH:30].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN1C(=O)N(C)CCC1>[OH:30][CH2:29][CH2:28][N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH3:26])[C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[CH2:17][C:11]3=[CH:10][N:9]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 18425451HCID 18425451, compound

Product 1

HCID 9865523HCID 9865523, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(piperidin-4-ylamino)-1-methyl-3-ortho-tolyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.1 g, 0.284 mmol) (prepared as described in Example 25), 2-bromoethanol (0.024 mL, 0.34 mmol), and triethylamine (0.047 mL, 0.34 mmol) in 10 mL of toluene and 1.5 mL of DMPU was heated at 100° C. for 17 hours. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 40:10:2 ethyl acetate/methanol/isopropylamine as eluant to give 70 mg (52%) of 7-[1-(2-hydroxyethyl)piperidin-4-ylamino]-1-methyl-3-ortho-tolyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel using 40:10:2 ethyl acetate/methanol/isopropylamine as eluant

Sources & evidence

ORD record
ord-ef4a6192460e4d368943b58a7a199ba8
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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