Hydrazine hydrate (1:1) → HCID 66553592, compound

HRID 390073Notes

Reaction equation

HRID 390073 reaction equation
[NH2:1][C:2]1[C:3]2[N:10](COCC3C=CC=CC=3)[CH:9]=[C:8]([CH2:20][NH:21][CH2:22][C@H:23]([OH:27])[CH2:24][S:25][CH3:26])[C:4]=2[N:5]=[CH:6][N:7]=1.O.NN>N.CO.[Pd]>[NH2:1][C:2]1[C:3]2[NH:10][CH:9]=[C:8]([CH2:20][NH:21][CH2:22][C@H:23]([OH:27])[CH2:24][S:25][CH3:26])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66953614HCID 66953614, compound

Product 1

HCID 66553592HCID 66553592, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21705897Ammonia methanolSolvent

Procedure

The product from Example 2.5 (0.08 g, 0.206 mmol) was dissolved in 7M NH3-MeOH solution (8 ml) and Pd black (80 mg) added followed by hydrazine hydrate (1.2 ml). The mixture was stirred for 40 mins, filtered and the solvent evaporated. The residue was chromatographed on silica gel (CH2Cl2-7M NH3 in MeOH, 85:15) to give(S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-(methylthio)propan-2-ol (0.042 g, 76%) as a colourless solid. [α]D20 −12.4 (c, 0.355, MeOH). 1H NMR (CD3OD), δ 8.16 (s, 1H), 7.48 (s, 1H), 4.00 (d, J=13.5 Hz, 1H), 3.92-3.84 (m, 2H), 2.85 (dd, J=12.2, 3.5 Hz, 1H), 2.65 (dd, J=12.2, 8.5 Hz, 1H), 2.55 (d, J=6.5 Hz, 2H), 2.10 (s, 3H). 13C NMR (CD3OD, referenced to the centre line of CD3OD at 49.0 ppm), δ 152.1, 150.9, 146.6, 129.1, 115.4, 114.2, 70.2, 54.6, 43.5, 40.4, 16.2. +ESMS Found 268.1241 (M+H)+ C11H18N5OS requires 268.1232.

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated
  3. customThe residue was chromatographed on silica gel (CH2Cl2-7M NH3 in MeOH, 85:15) to give(S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-(methylthio)propan-2-ol (0.042 g, 76%) as a colourless solid

Sources & evidence

ORD record
ord-74c9dccd5bd04033b7a14f65db84680e
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

Loading…