2-Thiophenecarbonyl chloride → HCID 86664813, compound

HRID 925545Notes

Reaction equation

HRID 925545 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([NH2:11])=[C:9]([Cl:12])[N:8]=[CH:7][N:6]=1)[CH:2]=[CH2:3].[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](Cl)=[O:19]>CN1C(=O)CCC1.O>[CH2:1]([NH:4][C:5]1[C:10]([NH:11][C:18]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)=[O:19])=[C:9]([Cl:12])[N:8]=[CH:7][N:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 2533706-chloro-4-N-prop-2-enylpyrimidine-4,5-diamine

Product 1

HCID 86664813HCID 86664813, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N*4*-Allyl-6-chloro-pyrimidine-4,5-diamine (0.20 g, 0.0011 mol) was taken in NMP (3 ml). Thiophene-2-carbonyl chloride (0.14 ml, 0.0013 mol) was added slowly at 0° C. and stirred for 2 hrs at same temperature. The reaction mixture was diluted with water (10 ml) and extracted with DCM (3×5 ml). The organic layer was washed with saturated NaHCO3 solution (10 ml), followed by brine (10 ml) and dried over Na2SO4. The solvent was removed to get thiophene-2-carboxylic acid (4-allylamino-6-chloro-pyrimidin-5-yl)-amide (0.281 g, 88%) as a pale yellow solid.

Workup

  1. extractionextracted with DCM (3×5 ml)
  2. washThe organic layer was washed with saturated NaHCO3 solution (10 ml)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-689c24c5e37847b09a0430692d9caa67
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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