Diisopropylethylamine → 6-isonicotinoyl-N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 930512Notes

Reaction equation

HRID 930512 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[CH2:23][NH:22][CH2:21][CH2:20][C:18]=3[N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:25]([N:22]1[CH2:21][CH2:20][C:18]2[N:19]=[C:14]([NH:13][C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:15]=[CH:16][C:17]=2[CH2:23]1)(=[O:32])[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12262826Isonicotinoyl chloride hydrochloride2×HCID 118970894N-(3,4,5-Trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 1189708956-isonicotinoyl-N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol) and isonicotinoyl chloride hydrochloride (56.1 mg, 0.32 mmol) in THF (2.0 mL) at room temperature was added N,N-diisopropylethylamine (0.157 mL, 0.90 mmol). After stirring for 3 hours at room temperature, an additional 21 mg of isonicotinoyl chloride hydrochloride was added and the reaction continued for 17 hours. The reaction was quenched with H2O, then treated with an EtOAc/saturated NaHCO3(aq) solution work-up to give an off-white solid. The solid was recrystallized from EtOAc/hexane to afford a white solid (115 mg, 91%).

Workup

  1. waitthe reaction continued for 17 hours
  2. customThe reaction was quenched with H2O
  3. additiontreated with an EtOAc/saturated NaHCO3(aq) solution work-up
  4. customto give an off-white solid
  5. customThe solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-58b6f67c72e04b9891f6c76e65ab5305
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

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