Water → 7-Acetylamino-4-methylthiopyrido[4,3-d]pyrimidine

HRID 1386191Notes

Reaction equation

HRID 1386191 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[N:15]=[CH:14][C:13]2[C:12]([S:16][CH3:17])=[N:11][CH:10]=[N:9][C:8]=2[CH:7]=1.CCN(CC)CC.O>C1COCC1>[C:1]([NH:5][C:6]1[N:15]=[CH:14][C:13]2[C:12]([S:16][CH3:17])=[N:11][CH:10]=[N:9][C:8]=2[CH:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 105376457-Acetylamino-4-methylthiopyrido[4,3-d]pyrimidineYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Acetyl chloride (0.70 mL, 9.84 mmol) is added to a solution of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (0.20 g, 1.04 mmol) (described in a previous experimental) and Et3N (1.51 mL, 10.8 mmol) in THF at 0° C., and then the mixture is stirred at 20° C. for 4 h. Water (50 mL) was added, then the solution was extracted with EtOAc (3×50 mL). Evaporation and chromatography on alumina (1% EtOH/CHCl3) yields 7-acetylamino-4-methylthiopyrido[4,3-d]pyrimidine (0.12 g, 49%) as a yellow solid, . 1H NMR (DMSO) δ 11.05 (1H, s), 9.30 (1H, s), 9.02 (1H, s), 8.38 (1H, s), 2.71 (3H, s), 2.18 (3H, s)

Workup

  1. customat 0° C.
  2. extractionthe solution was extracted with EtOAc (3×50 mL)
  3. customEvaporation and chromatography on alumina (1% EtOH/CHCl3)

Sources & evidence

ORD record
ord-25adf14b746c40938510d91dc2ea7320
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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