Hydrochloric Acid → 2-(6-Methoxy-pyrimidin-4-ylamino)-thiazole-5-carbonitrile

HRID 1241394Notes

Reaction equation

HRID 1241394 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.Cl[C:13]1[S:14][C:15]([C:18]#[N:19])=[CH:16][N:17]=1.Cl>O.C1COCC1>[CH3:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:13]2[S:14][C:15]([C:18]#[N:19])=[CH:16][N:17]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 7357314-Amino-6-methoxypyrimidineHCID 14852222-Chlorothiazole-5-carbonitrile

Product 1

HCID 219346832-(6-Methoxy-pyrimidin-4-ylamino)-thiazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A flame dried flask under argon gas was charged with sodium hydride (39 mg, 60% dispersion, 0.97 mmol) and 2 mL anhydrous THF. 6-Methoxy-pyrimidin-4-ylamine (55 mg, 0.44 mmol) was added slowly followed, after 10 minutes, by the addition of 2-chloro-thiazole-5-carbonitrile (76 mg, 0.53 mmol). After 1 hour, the reaction was diluted with water and adjusted to pH 7 with 1M HCl (aq). The resulting precipitate was filtered, washed with water and air dried. The resulting solid triturated with ether, sonucated, filtered and washed with ether. 1H-NMR (400 MHz, DMSO-d6) 12.40 (s, 1H), 8.68 (1H, s), 8.31 (1H, s), 6.42 (1H, s), 3.92 (s, 3H). M+1=234.2. mp 246–248.

Workup

  1. customA flame dried flask under argon gas
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water and air
  4. customdried
  5. customThe resulting solid triturated with ether
  6. filtrationfiltered
  7. washwashed with ether

Sources & evidence

ORD record
ord-5cf30abd1f444fb5b4dc5ab93178be4b
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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