Phosphorus oxybromide → 4-bromo-N-(4-morpholin-4-ylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 2091968Notes

Reaction equation

HRID 2091968 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[NH:15][C:16](=O)[C:17]4[CH:22]=[CH:21][NH:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.P(Br)(Br)([Br:26])=O.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[Br:26][C:16]1[C:17]2[CH:22]=[CH:21][NH:20][C:18]=2[N:19]=[C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:8][CH:9]=2)[N:15]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 81531DiisopropylethylamineHCID 136176028HCID 136176028, compound

Product 1

HCID 579913094-bromo-N-(4-morpholin-4-ylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-[(4-morpholin-4-ylphenyl)amino]-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one A (312 mg, 1 mmol), phosphorous oxybromide (717 mg, 2.5 mmol), and diisopropylethylamine (130 mg, 1 mmol) in anhydrous toluene (15 ml) was heated at reflux under N2 overnight. The mixture was cooled down to room temperature, and the solid was filtered, washed with sat. NaHCO3, water, and dried over MgSO4. The solvent was removed in vacuo to give the product 4-bromo-N-(4-morpholin-4-ylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine B (284 mg, 76%) as a black solid. This was clean and used as such without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 overnight
  3. filtrationthe solid was filtered
  4. washwashed with sat. NaHCO3, water
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-175650e8330c414f8891055bdc0758b2
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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