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Phosphorus pentachloride → 5-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-morpholin-4-yl-pyrimidin-4-ylamide

HRID 356654
Notes
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Reaction equation

HRID 356654 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:3]=1[O:4][C:5]1[C:6]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][N:24]=2)(=[O:22])=[O:21])=[N:7][C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:9][C:10]=1[CH2:11]O.P(Cl)(Cl)(Cl)(Cl)[Cl:39]>O=P(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:3]=1[O:4][C:5]1[C:6]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][N:24]=2)(=[O:22])=[O:21])=[N:7][C:8]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[N:9][C:10]=1[CH2:11][Cl:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178683755-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-morpholin-4-yl-pyrimidin-4-ylamide

Product 1

HCID 223778495-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-morpholin-4-yl-pyrimidin-4-ylamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 24813
Phosphorus oxychloride
Solvent

Procedure

0.2 g of the compound obtained in Example 38 in 3.5 ml of POCl3 was stirred with 0.083 g of PCl5 at 20° C. for 2 hours. Thereafter, the POCl3 was distilled off and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate (sic). The organic phase was washed with water, dried and the solvent was evaporated. The residue was chromatographed over silica gel with chloroform-methanol, thereafter recrystallized from dichloromethane-ethanol. 0.150 g of 5-isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-morpholin-4-yl-pyrimidin-4-ylamide, m.p. 205° C., was obtained.

Workup

  1. distillationThereafter, the POCl3 was distilled off
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate (sic)
  3. washThe organic phase was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed over silica gel with chloroform-methanol
  7. customrecrystallized from dichloromethane-ethanol

Sources & evidence

ORD record
ord-ae53e6594c4747139f01ab4a54ad25bf
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05837708

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes