Dimethylformamide → 2-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

HRID 1814013Notes

Reaction equation

HRID 1814013 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:6]=[C:5]([CH2:17]O)[CH:4]=1)[CH3:2].CN(C)C=O.P(Cl)(Cl)([Cl:26])=O>C(Cl)Cl>[Cl:26][CH2:17][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[N:8]=[C:7]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 225043012-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

Product 1

HCID 225042962-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (12-3, 0.146 g, 0.56 mmol) was stirred in anhydrous CH2Cl2 (2.5 mL) under N2. N,N-Dimethylformamide (0.043 mL, 0.56 mmol) was added followed by phosphorous oxychloride (0.209 mL, 2.24 mmol). After 2.5 hours, the reaction was concentrated and quenched by the addition of saturated NaHCO3 (aq). A precipitate formed which was filtered and washed with water to afford 2-{[4-(chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile as an orange solid. 1H NMR (DMSO-d6) δ 12.32 (s, 1H), 8.28 (s, 1H), 7.00 (d, 2H, J=3.66 Hz), 4.77 (s, 2H), 2.83 (q, 2H, J=7.63 Hz), 1.34 (t, 3H, J=7.63 Hz).

Workup

  1. concentrationthe reaction was concentrated
  2. customquenched by the addition of saturated NaHCO3 (aq)
  3. customA precipitate formed which
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-5d62dfdcdef94cb6bc0aa01880df777e
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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