Sodium Iodide → HCID 178418773, compound

HRID 480600Notes

Reaction equation

HRID 480600 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[NH2:13][C:14]1[CH:18]=[C:17]([CH:19]2[CH2:21][CH2:20]2)[NH:16][N:15]=1.C(N(CC)CC)C.[I-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:11]=[C:10]([NH:13][C:14]2[NH:15][N:16]=[C:17]([CH:19]3[CH2:21][CH2:20]3)[CH:18]=2)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 126028642,4-Dichloro-5,6,7,8-tetrahydroquinazoline

Product 1

HCID 178418773HCID 178418773, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (500 mg, 2.46 mmol) and 3-amino-5-cyclopropylpyrazole (303 mg, 2.46 mmol) in DMF (10 mL) is added triethylamine (0.357 mL, 2.56 mmol) followed by sodium iodide (368 mg, 2.46 mmol) and the reaction mixture is heated at 90° C. for 20 h. The reaction mixture is partitioned between ethyl acetate and aqueous saturated NaHCO3. The organic layer is washed with brine and evaporated in vacuo. The residue is purified by flash chromatography (SiO2, hexane/AcOEt gradient) to give (2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and aqueous saturated NaHCO3
  2. washThe organic layer is washed with brine
  3. customevaporated in vacuo
  4. customThe residue is purified by flash chromatography (SiO2, hexane/AcOEt gradient)

Sources & evidence

ORD record
ord-17ff2119edd2414f9c61c6b88614ecf8
Source dataset
uspto-grants-2003_11
Patent number
US06653300B2

Reaction notes

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