(Diethylamino)sulfur trifluoride → BW-4030W92, (-)-

HRID 1954933Notes

Reaction equation

HRID 1954933 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[C:4]([CH2:17]O)[N:3]=1.C(N(S(F)(F)[F:25])CC)C>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[C:4]([CH2:17][F:25])[N:3]=1

Participants

3

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 184039342,4-Diamino-5-(2,3-dichlorophenyl)-6-hydroxymethylpyrimidine

Product 1

HCID 9860692BW-4030W92, (-)-

Conditions

Temperature
-10 °C

Procedure

Fluorination of racemic 2,4-diamino-5-(2,3-dichlorophenyl)-6-hydroxymethyl pyrimidine can be effected using diethylaminosulphur trifluoride (DAST). That may be carried out in dichloromethane at, initially, -78° C. followed by warming to -10° C. for four and a half hours, to afford racemic 2,4-diamino-5-(2,3-dichlorophenyl)-6-fluoromethyl pyrimidine.

Workup

  1. custom-78° C.

Sources & evidence

ORD record
ord-e64a2494219c4133a7317a4bd30a68bb
Source dataset
uspto-grants-2000_09
Patent number
US06124308

Reaction notes

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