Thionyl Chloride → HCID 57803002, compound

HRID 2102363Notes

Reaction equation

HRID 2102363 reaction equation
S(Cl)([Cl:3])=O.O[C:6]1[C:7]2[C:14]([C:15]3[S:16][CH:17]=[CH:18][N:19]=3)=[CH:13][S:12][C:8]=2[N:9]=[CH:10][N:11]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:3][C:6]1[C:7]2[C:14]([C:15]3[S:16][CH:17]=[CH:18][N:19]=3)=[CH:13][S:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178518071HCID 178518071, compound

Product 1

HCID 57803002HCID 57803002, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
73 °C

Procedure

A mixture of thionyl chloride (15 ml, 200 mmol), 4-hydroxy-5-(thiazol-2-yl)thieno[2,3-d]pyrimidine (1.44 g, 12 mmol) and N,N-dimethylformamide (3 mL) was heated at 73° C. for 3 hours and then carefully poured into 200 mL of ice/water. The pH was adjusted to between 7 and 8 with sodium bicarbonate and then the product was extracted with ethyl acetate (2×450 mL). The organic fractions were combined, dried (MgSO4) and concentrated. The resulting residue was purified by column chromatography over silica gel using a gradient elution from 10 to 20% ethyl acetate in hexanes to give 0.825 g (53%) of 4-chloro-5-(thiazol-2-yl)thieno[2,3-d]pyrimidine as a brown solid. MS [M+H] 254.0, 1H NMR (400 MHz, 10% CD3OD/CDCl3) δ (ppm) 8.92 (s, 1H), 8.00 (d, J=3.2 Hz, 1H), 7.85 (s, 1H), 7.55 (d, J=3.2 Hz, 1H).

Workup

  1. extractionthe product was extracted with ethyl acetate (2×450 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting residue was purified by column chromatography over silica gel using
  5. washa gradient elution from 10 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3fb766a0c60f48b7ad9ddcf93241fb0c
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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