Sodium methanethiolate → 2-(Methylsulfanyl)-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 2268427Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.[CH3:26][S-:27].[Na+]>>[CH3:26][S:27][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1

Participants

Reactant 2

HCID 4378561Sodium methanethiolate

HCID 207091842-Chloro-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

Product 1

HCID 207091892-(Methylsulfanyl)-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineYield 92.2%

Procedure

The title compound was prepared by a similar method to preparation 7 from 2-chloro-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (17.5 g, 49 mmol) (preparation 41) and sodium thiomethoxide (7.2 g, 75 mmol). This gave the title compound (16.7 g) as a white solid.

Sources & evidence

ORD record: ord-56ed36503f044b758edc202cf67bc883
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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