Isopropylamine → 2-acetamido-4-(N-isopropylamino)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine

HRID 1025519Notes

Reaction equation

HRID 1025519 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7](C2N=CNN=2)[C:8]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[CH:27]([NH2:30])([CH3:29])[CH3:28]>O1CCOCC1>[C:1]([NH:4][C:5]1[N:6]=[C:7]([NH:30][CH:27]([CH3:29])[CH3:28])[C:8]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 178474430HCID 178474430, compound

Product 1

HCID 690791042-acetamido-4-(N-isopropylamino)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidineYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of the 2-acetamido-4-(1,2,4-triazolyl)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine of example 2 (70 mg) in dioxane (5 ml) was added isopropylamine (0.4 mmol). The reaction was stirred at room temperature for 24 hours. The solvents were evaporated in vacuo, yielding the crude title compound which was purified by preparative TLC on silica, using a mixture of methanol and dichloromethane, in a ratio of 10:90 as mobile phase, thus providing the title compound in 73% yield. The pure title compound was characterized by its mass spectrum as follows: MS (m/z): 340 ([M+H]+, 100).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customyielding the crude title compound which
  3. customwas purified by preparative TLC on silica
  4. additiona mixture of methanol and dichloromethane

Sources & evidence

ORD record
ord-9255a2db6ce149ababd4486365ebb536
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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