Sodium Hydroxide → HCID 131722285, compound

HRID 567768Notes

Reaction equation

HRID 567768 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21](OCC)=[O:22])=[CH:17][CH:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 21262623HCID 21262623, compound

Product 1

HCID 131722285HCID 131722285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3.53 g (9.0 mmol) of 4-(3-chloroanilino)-6-(4-ethoxycarbonylphenyl)-7H-pyrrolo[2,3-d]pyrimidine are suspended in 150 ml of THF. At 54° C., a total of 0.845 g (21.6 mmol) of lithium aluminum hydride are introduced in the course of 5 h. For working up, 1 ml of water, 2 ml of 1N sodium hydroxide solution and 1 ml of water, followed by 10 g of sodium sulfate, are added successively. The solid is filtered off and the filtrate is concentrated. The residue obtained is washed with methanol and diethyl ether and then dried. 4-(3-Chloroanilino)-6-(4-hydroxymethlyphenyl)-7H-pyrrolo[2,3-d]pyrimidine is obtained in colorless crystals; m.p.>250° C.; FAB-MS (M+H)+=351.

Workup

  1. additionare added successively
  2. filtrationThe solid is filtered off
  3. concentrationthe filtrate is concentrated
  4. customThe residue obtained
  5. washis washed with methanol and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-9e35985b60854b3f9b2c9aac3254c3e8
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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