Sodium hydride → HCID 25006711, compound

HRID 732144Notes

Reaction equation

HRID 732144 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][NH:17][C:12]3=[N:11][N:10]=2)=[CH:5][CH:4]=1.Cl[CH:19]([C:21]1[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[O:23][N:22]=1)[CH3:20].[NH4+].[Cl-]>CN(C=O)C.O>[Cl:32][C:28]1[CH:27]=[C:26]([C:24]2[O:23][N:22]=[C:21]([C@@H:19]([N:17]3[CH2:16][CH2:15][CH2:14][N:13]4[C:9]([C:6]5[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=5)=[N:10][N:11]=[C:12]34)[CH3:20])[N:25]=2)[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 578379793-(1-Chloroethyl)-5-(3-chlorophenyl)-[1,2,4]oxadiazoleHCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

Product 1

HCID 25006711HCID 25006711, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

NaH (716 mg, 29.8 mmol) was added slowly to a solution of 3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine (5.0 g, 24.8 mmol) in DMF (250 ml) under nitrogen. After 10 min a solution of 3-(1-chloroethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (6.0 g, 24.8 mmol) in DMF (200 ml) was added, followed by stirring o.n. at r.t. A sat NH4Cl solution was added followed by water. The mixture was extracted with EA and DCM. The combined organic extracts were washed with water and brine, dried and concentrated. Recrystallization from EA gave 2.24 g (22%) of the racemic product 8-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine. Separation on a Chiralpak AD column (100% 2-propanol) gave the title compound which eluted as second enantiomer. 1H NMR: 1.74 (d, 3 H) 2.17 (m, 2 H) 3.45 (m, 2 H) 4.10 (m, 2 H) 5.96 (m, 1 H) 7.44 (t, 1 H) 7.53 (m, 1 H) 7.59 (m, 2 H) 7.97 (m, 1 H) 8.08 (m, 1 H) 8.67 (d, 2 H)

Workup

  1. customat r.t
  2. extractionThe mixture was extracted with EA and DCM
  3. washThe combined organic extracts were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customRecrystallization from EA

Sources & evidence

ORD record
ord-5b2c2fb278004b3d87647c1f766468df
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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