Water → HCID 11694427, compound

HRID 1678260Notes

Reaction equation

HRID 1678260 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][S:5][C:6]1[C:11]([CH:12]=O)=[C:10]([Cl:14])[N:9]=[C:8]([NH2:15])[N:7]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[S:5][C:6]2[N:7]=[C:8]([NH2:15])[N:9]=[C:10]([Cl:14])[C:11]=2[CH:12]=1)=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 11499906HCID 11499906, compound

Product 1

HCID 11694427HCID 11694427, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of (2-amino-6-chloro-5-formyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester (Preparation #22e, 0.20 g, 0.76 mmol) in dioxane (7.6 mL) was added K2CO3 (0.21 g, 1.5 mmol). The resulting mixture was heated at about 100° C. overnight, cooled to room temperature and water (1 mL) added to dissolve base. The remaining solid was filtered and washed with MeOH to give 2-amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (0.16 g, 84%) as a pale yellow solid; RP-HPLC (Table 1, Method a) Rt 2.38 min; 1H NMR (d6-DMSO, 400 MHz) δ7.82 (s, 1H), 7.72 (br s, 2H), 3.86 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. dissolutionto dissolve base
  3. filtrationThe remaining solid was filtered
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-f25a8fb2fe2f41a9b2bef7c5a2c9719a
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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