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Triethylamine → 4-(2-Indanylamino)pyrido[2,3-d]pyrimidine

HRID 1581975
Notes
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Reaction equation

HRID 1581975 reaction equation
O[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.P(Cl)(Cl)(Cl)=O.[NH2:17][CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1.C(N(CC)CC)C>O1CCOCC1>[CH2:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26][CH:18]1[NH:17][C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 763102-AminoindaneHCID 178518041HCID 178518041, compound

Product 1

HCID 227196244-(2-Indanylamino)pyrido[2,3-d]pyrimidineYield 23%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

Using 4-hydroxypyrido[2,3-d]pyrimidine (150 mg, 1.0 mmol) (see J. Am. Chem. Soc., 77, 2256 (1955)), phosphorus oxychloride (1.0 ml), 2-aminoindan (270 mg, 2.0 mmol), triethylamine (1.4 ml, 10 mmol), and dry dioxane (5 ml), a similar procedure to Example 14 was carried out. The product obtained was purified by silica gel chromatography (ethyl acetate:methanol=19:1) to obtain the title compound (60 mg, 0.23 mmol) having the following physical properties:

Workup

  1. customThe product obtained
  2. customwas purified by silica gel chromatography (ethyl acetate:methanol=19:1)

Sources & evidence

ORD record
ord-eee0f49b4961426d9ddc5200a00ffe1f
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06734180B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes