Tetrahydrofuran → N5-[(4-fluorophenyl)methyl]-4,5-pyrimidinediamine

HRID 256635Notes

Reaction equation

HRID 256635 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[CH:4][N:3]=1.O1CCCC1.[AlH4-].[Li+]>O>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[N:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 28112Lithium aluminum hydride2×HCID 19785297N-(4-amino-5-pyrimidinyl)-4-fluorobenzamide

Product 1

HCID 86747348N5-[(4-fluorophenyl)methyl]-4,5-pyrimidinediamineYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 30 parts of N-(4-amino-5-pyrimidinyl)-4-fluorobenzamide and 360 parts of tetrahydrofuran were added portionwise 9.86 parts of lithium tetrahydroaluminate under nitrogen atmosphere. The mixture was stirred for 6 hours. Another portion of 10 parts of lithium tetrahydroaluminate was added portionwise and stirring was continued for 2 hours at room temperature. The reaction mixture was decomposed with water. The layers were separated. The aqueous phase was extracted with tetrahydrofuran. The combined organic layers were dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 18 parts (63.5%) of N5 -[(4-fluorophenyl)methyl]-4,5-pyrimidinediamine (interm. 12).

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours at room temperature
  3. customThe layers were separated
  4. extractionThe aqueous phase was extracted with tetrahydrofuran
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from acetonitrile
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-9d293193a96d4d9a8294992844f2828c
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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