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Water → 3-[2-(2,5-Dichloro-pyrimidin-4-ylamino)-5-morpholin-4-yl-phenoxy]-propionitrile

HRID 1687995
Notes
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Reaction equation

HRID 1687995 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:18]([O-])=O)=[C:11]([CH:17]=2)[O:12][CH2:13][CH2:14][C:15]#[N:16])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:28][C:29]1[N:34]=[C:33](Cl)[C:32]([Cl:36])=[CH:31][N:30]=1.O>[Pd].C(O)C>[Cl:28][C:29]1[N:34]=[C:33]([NH:18][C:10]2[CH:9]=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:17][C:11]=2[O:12][CH2:13][CH2:14][C:15]#[N:16])[C:32]([Cl:36])=[CH:31][N:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 672634833-(5-Morpholin-4-yl-2-nitro-phenoxy)-propionitrile

Product 1

HCID 866340643-[2-(2,5-Dichloro-pyrimidin-4-ylamino)-5-morpholin-4-yl-phenoxy]-propionitrileYield 66%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 702EthanolSolvent2×

Procedure

3-(5-Morpholin-4-yl-2-nitro-phenoxy)-propionitrile (209 mg, 0.754 mmol) and 10% Palladium on Carbon (50% Wet) (120 mg) in Ethanol (45 mL) was shaken under an atmosphere of Hydrogen (45 psi) for 1 h. The mixture was filtered, washing with ethanol, and Triethylamine (0.21 mL, 1.5 mmol) and 2,4,5-Trichloro-pyrimidine (0.13 mL, 1.1 mmol) were added to the filtrate. The mixture was stirred overnight, then poured into 100 mL water, then cooled. The solids were collected by filtration, to give 3-[2-(2,5-Dichloro-pyrimidin-4-ylamino)-5-morpholin-4-yl-phenoxy]-propionitrile as a purple solid (195 mg, 66%). 1H-NMR (CDCl3): 8.28 (d, 1H, J=8.0 Hz), 8.16 (s, 1H), 6.65 (d, 1H, J=8.0 Hz), 6.49 (s, 1H), 4.31 (t, 2H, J=5.2 Hz), 3.88 (t, 4H, J=4.1 Hz), 3.15 (t, 4H, J=4.1 Hz), 2.89 (t, 2H, J=5.2 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. additionwere added to the filtrate
  3. temperaturecooled
  4. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-d72d7a6886c2490f984d2222f5910c58
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148391B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes