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

HRID 1954930Notes

Reaction equation

HRID 1954930 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>ClCCl>[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

4

Reactant 2

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

Product 1

HCID 9860692BW-4030W92, (-)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

The fluorination is effected under conditions at which racemisation of the 6-hydroxymethyl and 6-fluoromethyl (-)enantiomers does not occur. The temperature should thus be less than 80° C., for example less than 50° C. Fluorination can be effected, for example, by the redaction of (-)-2,4-diamino-5-(2,3-dichlorophenyl)-6-hydroxymethyl pyrimidine with diethylaminosulphur trifluoride (DAST). That may be achieved in dichloromethane at -78° C. The solution is then stirred whilst allowing to warm to -10° C. over four and a half hours to give (-)2,4-diamino-5-(2,3-dichlorophenyl)-6-fluoromethyl pyrimidine.

Workup

  1. customthus be less than 80° C.
  2. customfor example less than 50° C

Sources & evidence

ORD record
ord-f7ab21116cde4d2fb730bc73c8dd80c8
Source dataset
uspto-grants-2000_09
Patent number
US06124308

Reaction notes

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