Phosphorus tribromide → HCID 178429477, compound

HRID 630062Notes

Reaction equation

P(Br)(Br)Br.Br[CH2:6][C:7]1[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=1.[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1>>[CH3:13][C:14]1[N:19]=[C:18]([S:20][CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=2)[N:17]=[C:16]([OH:21])[CH:15]=1

Participants

Reactant 3

HCID 24614Phosphorus tribromide

HCID 595895031256561-69-9

HCID 178429541HCID 178429541, compound

Product 1

HCID 178429477HCID 178429477, compoundYield 55%

Procedure

The title compound was prepared by following the procedure described for Example 55 from 1-methyl-1H-pyrazole-5-carbaldehyde to provide (1-methyl-1H-pyrazol-5-yl)methanol, which gave 5-(bromomethyl)-1-methyl-1H-pyrazole upon reaction with phosphorous tribromide. The reaction of 5-(bromomethyl)-1-methyl-1H-pyrazole and 6-methyl-2-sulfanylpyrimidin-4-ol provided 6-methyl-2-{[(1-methyl-1H-pyrazol-5-yl)methyl]sulfanyl}pyrimidin-4-ol as a white solid (0.742 g, 55% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 3.82 (s, 3H), 4.47 (s, 2H), 6.04 (bs, 1H), 6.23 (d, J=1.7 Hz, 1H), 7.29 (d, J=1.7 Hz, 1H), 8.19 (s, 1H); M+236.3.

Sources & evidence

ORD record: ord-4cc7fefa14844ad0a5c49106c3d9a70f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315521B2

Reaction notes

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