Tetrahydrofuran → HCID 178496595, compound

HRID 2074196Notes

Reaction equation

HRID 2074196 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([O:16][CH3:17])[CH2:12][CH2:11]2)[C:3]=1[NH2:18].C1C[O:22][CH2:21]C1>>[NH2:8][C:6]1[N:5]=[C:4]2[C:3]([NH:18][C:21](=[O:22])[N:9]2[C@H:10]2[CH2:11][CH2:12][C@H:13]([O:16][CH3:17])[CH2:14][CH2:15]2)=[C:2]([Cl:1])[N:7]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 178496608HCID 178496608, compound

Product 1

HCID 178496595HCID 178496595, compoundYield 67%

Procedure

To a solution of 6-chloro-N4-(trans-4-methoxycyclohexyl)pyrimidine-2,4,5-triamine (5.5 g, 20.36 mmol) in 300 mL of anhydrous THF (use oven dried glassware) was added 1,1-carbonyldiimidazole (newly opened bottle, 19.8 g, 122.2 mmol, 6 equiv.) as a solid, in portions. The reaction mixture was stirred at room temperature for 2 h (completion of the reaction checked by HPLC and MS). The solvent was removed in vacuo. Water (250 mL) was added to the residue and the mixture stirred at room temperature for 10 min. The solid formed was filtered under vacuum, washed with cold water and thoroughly dried to give the desired product as a brown solid (67% yield), which was used in the next step without further purification. MS (EI) m/z 298 (MH)+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionWater (250 mL) was added to the residue
  3. stirringthe mixture stirred at room temperature for 10 min
  4. customThe solid formed
  5. filtrationwas filtered under vacuum
  6. washwashed with cold water
  7. customthoroughly dried

Sources & evidence

ORD record
ord-cb36c38babaf4f5d81707102f32cba39
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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