Iodoethane → HCID 19883210, compound

HRID 846821Notes

Reaction equation

HRID 846821 reaction equation
[H-].[Na+].[ClH:3].Cl.[NH2:5][C:6]1[N:7]=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:9]2[CH2:15][NH:14][CH2:13][CH2:12][C:10]=2[N:11]=1.I[CH2:24][CH3:25]>CN(C)C=O>[ClH:22].[ClH:3].[NH2:5][C:6]1[N:7]=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:9]2[CH2:15][N:14]([CH2:24][CH3:25])[CH2:13][CH2:12][C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 19883214HCID 19883214, compound

Product 1

HCID 19883210HCID 19883210, compoundYield 158.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydride (12.7 g, 320 mmol), washed three times pentanes, in dimethylformamide (200 mL) was treated with 2-amino-4-(4-chlorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride (35.3 g, 110 mmol). The mixture was stirred at room temperature for 2 hours, and iodoethane (8.8 mL, 110 mmol) was added. The mixture was stirred at room temperature overnight, quenched with water and the resulting precipitate was collected by filtration to give 31.5 g (79%) of 2-amino-4-(4-chlorophenyl)-6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride. m.p.>260° C. MS: 289 (MH+). IR(KBr): 3224, 2641, 2311, 1623 cm-1.

Workup

  1. washwashed three times pentanes
  2. stirringThe mixture was stirred at room temperature overnight
  3. customquenched with water
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-5dd5561f7fce482e986de994e9907a6b
Source dataset
uspto-grants-1992_08
Patent number
US05137890

Reaction notes

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