Morpholine → 2-Chloro-4-morpholinofuro[3,2-d]pyrimidine

HRID 2403357Notes

Reaction equation

HRID 2403357 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidine

Product 1

HCID 568337412-Chloro-4-morpholinofuro[3,2-d]pyrimidineYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dichlorofuro[3,2-d]pyrimidine (23 mg, 1.0 eq) was suspended in methanol (1.7 ml) and treated with morpholine (0.09 ml, 4.0 eq). Reaction mixture was stirred at room temperature for 2 h, before being quenched with saturated aq. NaHCO3. Mixture was extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated to yield 2-chloro-4-morpholinofuro[3,2-d]pyrimidine (14 mg, 48%) which was used in the next reaction without further purification.

Workup

  1. customReaction mixture
  2. custombefore being quenched with saturated aq. NaHCO3
  3. extractionMixture was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a926e7eb16a04445a5617c44194a2719
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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