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

HRID 2292519Notes

Reaction equation

HRID 2292519 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, (-)-Yield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 2,4-diamino-5-(2,3-dichlorophenyl)-6-hydroxymethylpyrimidine (185 mg; 1 mmol) in dry dichloromethane (25 ml), under nitrogen at -70° C., was added dropwise diethylaminosulphur trifluoride (263 μl; 2 mmol). The mixture was allowed to warm to 0° C. and kept at this temperature for 4 hours. After cooling to -70° C. the mixture was quenched with aqueous sodium bicarbonate, extracted with dichloromethane (2×50 ml), washed with saturated brine and dried (MgSO4). Concentration gave a colourless gum (0.2 g). Chromatography on silica gel, eluting with 0.01:1:19 Et3N:MeOH:CH2Cl2 gave the desired product which was triturated with CCl4 and dried in vacuo. 111 mg, mp. 224°-6° C.

Workup

  1. temperatureAfter cooling to -70° C. the mixture
  2. customwas quenched with aqueous sodium bicarbonate
  3. extractionextracted with dichloromethane (2×50 ml)
  4. washwashed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration

Sources & evidence

ORD record
ord-57e1f8d1c1454acfa747b1aa12d7f208
Source dataset
uspto-grants-1997_11
Patent number
US05684005

Reaction notes

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