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

HRID 1041653Notes

Reaction equation

HRID 1041653 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

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 23938PalladiumCatalystHCID 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-481599fae20c4d98b7a758b63dad0a9c
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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