Phenylphosphonic dichloride → HCID 18456541, compound

HRID 1272385Notes

Reaction equation

HRID 1272385 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](O)=[N:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11][C:10]=2[CH:9]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(Cl)([Cl:38])=O)C=CC=CC=1>>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:38])=[N:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11][C:10]=2[CH:9]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 69990Phenylphosphonic dichlorideHCID 178517784HCID 178517784, compound

Product 1

HCID 18456541HCID 18456541, compoundYield 66%

Conditions

Temperature
150 °C

Procedure

A mixture of 669 mg (1.68 mmol) of 7,8-dibenzyl-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ol and 1.2 mL of phenylphosphonic dichloride was heated in a sealed tube at 150° C. for 2.5 h. The mixture was cooled to ˜100° C., then poured into crushed ice, washing with ethyl acetate. The resultant biphasic mixture was neutralized with solid sodium bicarbonate to ˜pH 8 with vigorous stirring. The ethyl acetate layer was removed. The aqueous layer was extracted with ethyl acetate. The combined organic phases were washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried, and concentrated to give a red, viscous oil. Purification by Biotage chromatography (silica gel, 5% ethyl acetate/hexane) gave 464 mg (66%) of the title compound as a yellow solid. LC-MS 418.0 (M+1).

Workup

  1. temperatureThe mixture was cooled to ˜100° C.
  2. additionpoured
  3. custominto crushed ice
  4. washwashing with ethyl acetate
  5. customThe ethyl acetate layer was removed
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic phases were washed sequentially with saturated aqueous sodium bicarbonate solution and brine
  8. customdried
  9. concentrationconcentrated
  10. customto give a red, viscous oil
  11. customPurification by Biotage chromatography (silica gel, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0b9b794e2cc0473d8ebe4de677fe2277
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

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