Phosgene → HCID 22027861, compound

HRID 1791132Notes

Reaction equation

HRID 1791132 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][CH2:26][CH2:27][OH:28])[CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C1COCC1>[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:26][CH2:27][O:28][C:1]4=[O:2])[CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 19689608HCID 19689608, compound

Product 1

HCID 22027861HCID 22027861, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phosgene in toluene (1.9 ml of a 20% commercial solution, 3.5 mmol) is added within five minutes to a solution of 2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-ylamino}-ethanol (0.88 g, 2.6 mmol) and triethylamine (1.7 ml, 11.7 mmol) in absolute THF (20 ml) at 50° C. After stirring the resulting suspension for one hour at room temperature it is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced presssure. The residue is purified by silicagel chromatography to give the title compound, m.p. 162–163° C.

Workup

  1. customis partitioned between ethyl acetate and water
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced presssure
  6. customThe residue is purified by silicagel chromatography

Sources & evidence

ORD record
ord-ea1ad38d1a944a9783b596f002b9656b
Source dataset
uspto-grants-2006_07
Patent number
US07074787B2

Reaction notes

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