Sodium Hydroxide → 5-(2-Amino-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole

HRID 2264601Notes

Reaction equation

HRID 2264601 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1.[BH3-]C#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 219492624-(1H-5-indolyloxy)-2-pyrimidinamine

Product 1

HCID 675302915-(2-Amino-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 160 mg (0.70 mMol) of 5-(2-amino-pyrimidin-4-yloxy)-1H-indole in 4 ml acetic acid is cooled to 10-15° C. Then 222 mg (3.5 mMol) NaBH3CN are added. After 1 h stirring at rt, 8 g of ice are added. Then the mixture is made basic by addition of 1 N NaOH and extracted three times with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated at rt in vacuo: MS: [M+1]+=229.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe organic layers are washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at rt in vacuo

Sources & evidence

ORD record
ord-59d0731eebbc4225b3ea77f6279d2465
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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