Chloride → HCID 11670829, compound

HRID 33981Notes

Reaction equation

HRID 33981 reaction equation
CS(C)=O.[Cl-].[OH:6][CH:7]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:8][N:9]1[C:14]2=[N:15][C:16]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:18](=[O:19])[N:13]2[CH2:12][CH2:11][CH2:10]1.CCN(CC)CC>C(Cl)Cl>[O:6]=[C:7]([CH2:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[CH2:8][N:9]1[C:14]2=[N:15][C:16]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:18](=[O:19])[N:13]2[CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 597965069-(2-Hydroxy-4-phenyl-butyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 11670829HCID 11670829, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of DMSO (0.25 mL, 3.5 mmol) in CH2Cl2 (10 mL) at −78 C was treated with a solution of oxallyl chloride (2N in CH2Cl2, 0.8 mL, 1.6 mmol) dropwise. After stirring for 15 min, a solution of 9-(2-hydroxy-4-phenyl-butyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (227 mg, 0.43 mmol) in CH2Cl2 (15 mL) was added. The mixture was stirred at −60 C for 15 min before a solution of Et3N (0.5 mL, 3.6 mmol) in CH2Cl2 (3 mL) was added. The reaction mixture was allowed to warm to room temperature overnight and was washed with NaHCO3 (aq). The organic layer was dired (Na2SO4), and concentrated. The residue was eluted on silica gel with 0-5% (2N NH3-MeOH in CH2Cl2) to afford the product as a light yellow solid (148 mg, 63%). M+1 519.

Workup

  1. additionwas added
  2. washwas washed with NaHCO3 (aq)
  3. concentrationconcentrated
  4. washThe residue was eluted on silica gel with 0-5% (2N NH3-MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0e3c6dd3a80d4d95964ac69d7cb58630
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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