Formaldehyde → 5-(4-Cyclopropylmethoxy-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine

HRID 48461Notes

Reaction equation

HRID 48461 reaction equation
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH:9]1([CH2:12][O:13][C:14]2[CH:22]=[C:21]([CH2:23][C:24]3[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=3)[CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[CH2:32][CH3:33])[CH2:11][CH2:10]1>C(O)(=O)C.O>[CH:9]1([CH2:12][O:13][C:14]2[CH:22]=[C:21]([CH2:23][C:24]3[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=3)[CH:20]=[C:19]3[C:15]=2[C:16]([CH2:1][N:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[CH:17][N:18]3[CH2:32][CH3:33])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 69922707HCID 69922707, compound

Product 1

HCID 699233515-(4-Cyclopropylmethoxy-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamineYield 69.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Formaldehyde (35% aqueous solution, 41 μL, 0.48 mmol) was added at room temperature to a solution of morpholine (142 mg, 1.60 mmol) in acetic acid (1.6 mL) and water (0.2 mL). After 10 min 5-(4-cyclopropylmethoxy-1-ethyl-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine (Example 7a; 134 mg, 0.40 mmol) was added, then after 45 min the solution was concentrated. 1M aqueous sodium hydroxide solution (10 mL) was added to the viscous residue, then the suspension formed was stirred at room temperature for 1 h, the solvent was removed and the gummy precipitate washed with water and dried to afford the title compound (121 mg, 69%). Off-white solid.

Workup

  1. concentrationafter 45 min the solution was concentrated
  2. addition1M aqueous sodium hydroxide solution (10 mL) was added to the viscous residue
  3. customthe suspension formed
  4. customthe solvent was removed
  5. washthe gummy precipitate washed with water
  6. customdried

Sources & evidence

ORD record
ord-327338d620544ef28f985eb4653c28db
Source dataset
uspto-grants-2004_03
Patent number
US06703397B2

Reaction notes

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