Indole → 2-Methylthio-4-[indol-1-yl]pyrimidine

HRID 429297Notes

Reaction equation

HRID 429297 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1.[N:21]1([C:30]2[N:35]=[C:34](SC)C=CN=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]1.O[O:39][S:40]([O-:42])=O.[K+]>>[CH3:20][S:19][C:15]1[N:16]=[C:17]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:18]=[CH:13][N:14]=1.[CH3:13][S:40]([C:34]1[N:35]=[C:30]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)[CH:3]=[CH:2][N:1]=1)(=[O:42])=[O:39]

Participants

7

Reactant 5

HCID 798IndoleHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 183543842-[Indol-1-yl]-4-methylthiopyrimidineHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 183543622-Methylthio-4-[indol-1-yl]pyrimidineHCID 18354396HCID 18354396, compound

Procedure

2-Methylthio-4-[indol-1-yl]pyrimidine was prepared from indole (1.00 g), NaH (220 mg), and 4-chloro-2-methylthiopyrimidine (0.9 mL) according to the procedure described in EXAMPLE 1, Step A. The title compound was prepared from 2-[indol-1-yl]-4-methylthiopyrimidine (2.11 g) and oxone (10.5 g) according to the procedure described in EXAMPLE 1, Step B. Mass spectrum (ESI) 274.0 (M+1).

Sources & evidence

ORD record
ord-4e0967b7e9c0493ea9a859cd78396d5e
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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