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

HRID 390813Notes

Reaction equation

HRID 390813 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 37 (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 38 (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-af65e09f594f4e208c058c8d92086afc
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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