Phosphorus oxychloride → HCID 86616700, compound

HRID 254170Notes

Reaction equation

HRID 254170 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[N:5]=[C:4]([NH2:13])[N:3]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[N:5]=[C:4]([NH2:13])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178508971HCID 178508971, compound

Product 1

HCID 86616700HCID 86616700, compoundYield 60%

Conditions

Temperature
120 °C

Procedure

A suspension of the 4-hydroxy-6-(2-thiazolyl)pyrimidine-2-amine (2.64 g, 13.6 mmol) in POCl3 (30 mL) was heated at 120° C. for 3 h, cooled and concentrated in vacuo. The resulting brown solid was added to ice/water (200 g), basified with NH4OH (8 mL), filtered and purified by chromatography [SiO2; EtOAc:isohexane (2:3-1:0)] to give the title compound (1.73 g, 60%) as a pale yellow solid; NMR δH (400 MHz, DMSO) 7.22 (1H, s), 7.40 (2H, br s), 8.01 (1H, d, J 3.2 Hz) and 8.07 (1H, d, J 3.2 Hz); M/Z 213, 215 (M+H)+

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionThe resulting brown solid was added to ice/water (200 g)
  4. filtrationfiltered
  5. custompurified by chromatography [SiO2; EtOAc:isohexane (2:3-1:0)]

Sources & evidence

ORD record
ord-e56b097ed5b64eed97f805d672dae252
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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