Dimethylformamide → 2-(4-Chloromethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

HRID 1813998Notes

Reaction equation

HRID 1813998 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([NH:10][C:11]2[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=2)[CH:4]=1.CN(C)C=O.P(Cl)(Cl)([Cl:25])=O>ClCCl>[Cl:25][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([NH:10][C:11]2[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 225042912-(4-Hydroxymethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Product 1

HCID 225043102-(4-Chloromethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Hydroxymethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (9-8, 0.400 g, 1.62 mmol) was stirred in 5 mL of anhydrous dichloromethane. N,N-Dimethylformamide (0.125 mL, 1.62 mmol) was added followed by the addition of phosphorous oxychloride (0.151 mL, 1.62 mmol). After 2 hours the reaction was concentrated in vacuo. Half-saturated NaHCO3 (aq) was added and the resulting precipitate was filtered and washed with water. Air drying provided the titled product, 9-9 contaminated with BINAP oxide. 1H NMR (DMSO-d6) δ 8.24 (s, 1H), 8.22 (s, 1H), 7.17 (s, 1H), 4.80 (s, 2H), 2.28 (s, 3H).

Workup

  1. concentrationAfter 2 hours the reaction was concentrated in vacuo
  2. additionHalf-saturated NaHCO3 (aq) was added
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water
  5. customAir drying

Sources & evidence

ORD record
ord-48e4f00458644a9a837e538e24cb3dff
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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