Dichloromethane → HCID 66553591, compound

HRID 390070Notes

Reaction equation

HRID 390070 reaction equation
C(OC[N:10]1[C:18]2[C:17](Cl)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:20][NH:21][C:22]([CH2:27][S:28][CH3:29])([CH2:25][OH:26])[CH2:23][OH:24])=[CH:11]1)C1C=CC=CC=1.Cl.[NH2:31]N.ClCCl>N.[Pd]>[NH2:31][C:17]1[C:18]2[NH:10][CH:11]=[C:12]([CH2:20][NH:21][C:22]([CH2:27][S:28][CH3:29])([CH2:25][OH:26])[CH2:23][OH:24])[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 115031Hydrazinium chlorideHCID 86651324HCID 86651324, compound

Product 1

HCID 66553591HCID 66553591, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 222AmmoniaSolvent2×

Procedure

To a suspension of 2-((5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(methylthiomethyl)propane-1,3-diol (9.0 mg, 0.037 mmol) and palladium-black (10 mg) in 7 M methanolic ammonia (2 mL) was added hydrazine hydrochloride (0.250 mL, 6.87 mmol) dropwise. After 1 h at ambient temperature the reaction was virtually complete by TLC (dichloromethane:7 M methanolic ammonia, 3:1, visualised with UV and Erlichs). The supernatant solution was filtered through a small pad of celite and the palladium was washed twice with methanol and also filtered through celite. The combined filtrates were concentrated under reduced pressure and the resulting residue triturated with chloroform and dichloromethane. Lyophilization of the residue gave 2-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(methylthiomethyl)propane-1,3-diol (4 mg, 63%) as a white solid. 1H NMR (D2O) δ 8.16 (s, 1H), 7.58 (s, 1H), 4.12 (s, 2H), 3.79-3.70 (m, 4H), 2.85 (s, 2H), 2.15 (s, 3H). +ESMS Found 298.1346 (M+H+) C12H20N5O2S requires 298.1338.

Workup

  1. filtrationThe supernatant solution was filtered through a small pad of celite
  2. washthe palladium was washed twice with methanol
  3. filtrationalso filtered through celite
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customthe resulting residue triturated with chloroform and dichloromethane

Sources & evidence

ORD record
ord-0a710ee87cc34635a7f4fe47cf44d218
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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