Potassium Carbonate → 2-(6-Chloro-4-hydroxymethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

HRID 1814007Notes

Reaction equation

HRID 1814007 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C:16]2[S:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)[CH:9]=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[Cl:14][C:12]1[N:11]=[C:10]([NH:15][C:16]2[S:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)[CH:9]=[C:8]([CH2:7][OH:6])[CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 1317248192-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-pyridin-2-ylamino]-thiazole-5-carbonitrile

Product 1

HCID 225043052-(6-Chloro-4-hydroxymethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-pyridin-2-ylamino]-thiazole-5-carbonitrile (11-6) was dissolved in 5 mL of THF. HF-pyr (Aldrich), 0.5 mL was added and the reaction was stirred at room temperature. After 1.5 hours the reaction was diluted with water and adjuted to pH 7 by the gradual addition of solid K2CO3. The mixture was extracted 3× with DCM. Large amounts of solid were suspended in the DCM extracts so the extracts were filtered and washed with DCM to afford the desired product, 11-7. 1H NMR (DMSO-d6) δ 12.49 (s, 1H), 8.30 (s, 1H), 7.09 (s, 1H), 7.06 (s, 1H), 5.59 (t, 1H, J=5.8 Hz), 4.55 (d, 2H, J=5.5 Hz).

Workup

  1. additionHF-pyr (Aldrich), 0.5 mL was added
  2. extractionThe mixture was extracted 3× with DCM
  3. filtrationwere filtered
  4. washwashed with DCM

Sources & evidence

ORD record
ord-7feb5e33fe4a42e889f747e32939542d
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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