Indoline → 4-(Indolin-1-yl)pyrimidin-2-amine

HRID 1588481Notes

Reaction equation

HRID 1588481 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10328IndolineHCID 2233322-Amino-4-chloropyrimidine

Product 1

HCID 197541384-(Indolin-1-yl)pyrimidin-2-amineYield 89.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2-amino-4-chloropyrimidine (1.3 g; 10 mM) in dioxan (30 ml) was treated with indoline (2.4 g; 20 mM) and the mixture was heated for 18 hours at 95°-100° C. The precipitated product was separated from the cooled mixture by filtration and suspended in a mixture of 2-propanol (30 ml) and a solution of potassium hydroxide flake (6 g) in water (10 ml). This mixture was stirred and heated at 95°-100° C. for one hour. The hot 2-propanol solution was separated from the aqueous layer and allowed to cool. The solid product was recrystallised from 2-propanol to give 2-amino-4-(indolin-1-yl)pyrimidine as a solid (1.9 g, 89.6%), m.p. 177°-179° C.; microanalysis, found: C,62.2; H,6.2; N,23.8%; C12H12N4.H2O requires: C, 62.6; H,6.1; N,24.3%.

Workup

  1. temperaturethe mixture was heated for 18 hours at 95°-100° C
  2. customThe precipitated product was separated from the cooled mixture by filtration
  3. additionsuspended in a mixture of 2-propanol (30 ml)
  4. temperatureheated at 95°-100° C. for one hour
  5. customThe hot 2-propanol solution was separated from the aqueous layer
  6. temperatureto cool
  7. customThe solid product was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-6313c84b66c44c20b929192330c8d51c
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Reaction notes

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