2-(Dimethylamino)ethanol → HCID 10255293, compound

HRID 639393Notes

Reaction equation

HRID 639393 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[C:22]([C:26]5[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=5)=[N:23][NH:24][CH:25]=4)[CH:18]=[CH:17][N:16]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][N:23]1[C:22]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[C:21]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[CH:13][CH:12]=3)[N:20]=2)[CH:25]=[N:24]1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178424075HCID 178424075, compound

Product 1

HCID 10255293HCID 10255293, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the suspension of 90 mg (0.211 mMol) of [4-(4-methyl-piperazin-1-yl)-phenyl]-[4-(3-p-tolyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine (Example 25) in 4.5 mL of THF is added 38 mg (0.426 mMol) of 2-dimethylamino-ethanol (Fluka) and 122 mg (0.465 mMol) of triphenylphosphine (Fluka). The yellowish suspension is cooled to 0° C. and treated with 81 mg (0.465 mMol) of DEAD*. The mixture is stirred without cooling for 17 h, followed by heating for 24 h at 60° C. After cooling to rt, the reaction mixture is filtered and washed with 5 mL of THF. The filtrate is concentrated under reduced pressure and the crude product is purified by repeated chromatography on silica gel, eluting with CH2Cl2/MeOH (9:1) and CH2Cl2/MeOH/H2O 70:30:5 to obtain the title compound as beige crystals.

Workup

  1. temperaturewithout cooling for 17 h
  2. temperatureby heating for 24 h at 60° C
  3. temperatureAfter cooling to rt
  4. filtrationthe reaction mixture is filtered
  5. washwashed with 5 mL of THF
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe crude product is purified
  8. washeluting with CH2Cl2/MeOH (9:1) and CH2Cl2/MeOH/H2O 70:30:5

Sources & evidence

ORD record
ord-365afb0b7c534353afaee46c1782a18a
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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