Sodium Hydroxide → HCID 59408900, compound

HRID 1422494Notes

Reaction equation

HRID 1422494 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:13]2[N:21]=[C:20]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)[N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3[C@H:29]([CH3:39])[CH2:30][O:31]CC2C=CC=CC=2)=[CH:2]1.B(Cl)(Cl)Cl.[OH-].[Na+]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:13]2[N:21]=[C:20]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)[N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3[C@H:29]([CH3:39])[CH2:30][OH:31])=[CH:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 68667926HCID 68667926, compound

Product 1

HCID 59408900HCID 59408900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)—N-(2-(1H-indol-3-yl)ethyl)-9-(1-(benzyloxy)propan-2-yl)-2-(5-fluoropyridin-3-yl)-9H-purin-6-amine (b) (0.15 g, 0.29 mmol) in DCM (10 ml) was treated with BCl3 (1M, 2.9 ml, 2.9 mmol) in DCM (10 ml) at −78° C. for 2 hr. 1N aqueous sodium hydroxide solution was added, and the mixture was extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated and the residue was purified by silica gel column chromatography (5% MeOH in DCM eluant) to provide the title compound. MS m/z 432.2 (M+1).

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel column chromatography (5% MeOH in DCM eluant)

Sources & evidence

ORD record
ord-7ccdca804d2f4dddb8c4208d0ad030d7
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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