Potassium Carbonate → HCID 23321117, compound

HRID 280702Notes

Reaction equation

HRID 280702 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]#C)[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[CH:4][N:3]=1.[C:24](=O)([O-])[O-].[K+].[K+]>S1(CCCC1)(=O)=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[CH:24]=[C:17]([CH3:18])[O:16][C:14]=3[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 128498032,4-Diamino-5-[3,4-dimethoxy-5-(2-propynyloxy)benzyl]pyrimidine

Product 1

HCID 23321117HCID 23321117, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A mixture of 2,4-diamino-5-[3,4-dimethoxy-5-(2-propynyloxy)benzyl]pyrimidine (1.18 g, 3.75 mmol), potassium carbonate (0.518 g, 3.75 mmol) and sulfolane (10 mL) was heated to 220°-230° under nitrogen over a period of 20 minutes and then maintained at this temperature for an additional 15 minutes. The resulting dark mixture was cooled and the precipitate was adsorbed on silica gel. The title compound was eluted with MeOH:CH2Cl2 /1:9 as an off-white powder, after recrystallization from 95% ethanol; mp 209°-212°. Anal. Calcd for C16H18N4O3.1/2H2O: C, 59.43; H, 5.92; N, 17.33. Found: C, 59.22; H, 5.97; N, 17.31.

Workup

  1. temperaturewas heated to 220°-230° under nitrogen over a period of 20 minutes
  2. temperaturemaintained at this temperature for an additional 15 minutes
  3. temperatureThe resulting dark mixture was cooled
  4. washThe title compound was eluted with MeOH
  5. customCH2Cl2 /1:9 as an off-white powder, after recrystallization from 95% ethanol

Sources & evidence

ORD record
ord-27da8cd67b71426da250eb87c432f894
Source dataset
uspto-grants-1986_05
Patent number
US04590271

Reaction notes

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