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Morpholine → 5-[4-(2-morpholinomethylphenoxy)phenyl]-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51487
Notes
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Reaction equation

HRID 51487 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:25]=[CH:24][C:14]([O:15][C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[CH:18]=O)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:26]3[CH2:30][CH2:29][O:28][CH2:27]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[O:34]1[CH2:35][CH2:36][N:31]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[O:15][C:14]2[CH:13]=[CH:12][C:11]([C:10]3[C:3]4[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=4[N:8]([CH:26]4[CH2:30][CH2:29][O:28][CH2:27]4)[CH:9]=3)=[CH:25][CH:24]=2)[CH2:32][CH2:33]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 865890032-[4-(4-amino-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]benzaldehyde

Product 1

HCID 227363765-[4-(2-morpholinomethylphenoxy)phenyl]-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents

1
HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-[4-(4-amino-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]benzaldehyde (0.15 g), morpholine (64 mg), sodium triacetoxyborohydride (117 mg) and 1,2 dichloroethane (5 ml) was stirred at ambient temperature for 18 hours. Saturated aqueous sodium bicarbonate solution was added and the mixture was filtered through an EMPORE® cartridge. The filtrate was evaporated and the residue was dissolved in dichloromethane (5 ml) and then tris(2-aminoethyl)amine-polymer bound (0.3 g) and 2 drops of glacial acetic acid were added and the mixture was stirred at ambient temperature overnight. The polymer was removed by filtration and washed with dichloromethane and then with methanol. The combined organic filtrate and washings were evaporated under reduced pressure to give an oil which was triturated with diethyl ether/ethyl acetate with warming to dissolve the solid and then the solution was cooled in ice and filtered to give 5-[4-(2-morpholinomethylphenoxy)phenyl] -7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 169-171° C.

Workup

  1. filtrationthe mixture was filtered through an EMPORE® cartridge
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  4. additionwere added
  5. stirringthe mixture was stirred at ambient temperature overnight
  6. customThe polymer was removed by filtration
  7. washwashed with dichloromethane
  8. customThe combined organic filtrate and washings were evaporated under reduced pressure
  9. customto give an oil which
  10. customwas triturated with diethyl ether/ethyl acetate
  11. temperaturewith warming
  12. dissolutionto dissolve the solid
  13. temperaturethe solution was cooled in ice
  14. filtrationfiltered

Sources & evidence

ORD record
ord-1a8edf61788143b88d2c5384b5067193
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes