Diglyme → HCID 22160583, compound

HRID 1089281Notes

Reaction equation

HRID 1089281 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]=[O:11])=[CH:4][N:3]=1.[CH3:12][C:13]1([CH3:22])[O:18][CH2:17][CH:16](NOC)[CH2:15][O:14]1.C([N:26](C(C)C)CC)(C)C.COCCOCC[O:39][CH3:40]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:26][O:39][CH2:40][CH:16]2[CH2:15][O:14][C:13]([CH3:12])([CH3:22])[O:18][CH2:17]2)[C:5]([NH:9][CH:10]=[O:11])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 8150DiglymeHCID 81531DiisopropylethylamineHCID 22160577HCID 22160577, compoundHCID 22160579HCID 22160579, compound

Product 1

HCID 22160583HCID 22160583, compoundYield 84%

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-dichloro-5-formamidopyrimidine (2.5 g, 13.0 mmol), 2,2-dimethyl-1,3-dioxan-5-yl-methoxyamine (13.6 mmol), diisopropylethylamine (4.5 ml, 25.8 mmol) and 2-methoxyethyl ether (50 ml) was heated at 100° C. for 4.5 hours. The suspension was cooled and evaporated under reduced pressure. The residue was chromatographed on silica gel (eluted with chloroform-methanol, 20:1), yielding the title compound (3.45 g, 84%).

Workup

  1. temperatureThe suspension was cooled
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel (eluted with chloroform-methanol, 20:1)

Sources & evidence

ORD record
ord-8846f2a97829417ba20e703104e73d67
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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