Thionyl Chloride → 5-(4-(Chloromethyl)-2-methoxybenzyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

HRID 1617156Notes

Reaction equation

HRID 1617156 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[N:11]=[C:10]([CH3:12])[C:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][C:15]=2[O:22][CH3:23])=[C:8]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N:7]=1>C(Cl)Cl>[Cl:3][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:9]2[C:8]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:7][C:6]([NH2:5])=[N:11][C:10]=2[CH3:12])=[C:15]([O:22][CH3:23])[CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66819929(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)methanol

Product 1

HCID 689586835-(4-(Chloromethyl)-2-methoxybenzyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.239 mL) was added portionwise to a solution of the product from step (v) (0.94 g) in DCM (20 mL) under nitrogen. The resulting solution was stirred at rt for 1 h. The solvent was evaporated under reduced pressure to give the subtitle compound as a colourless gum 0.99 g that was used without purification.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a9e2caf12bd14668835bd5b7eef5d6ce
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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