Sodium hydride → HCID 56598119, compound

HRID 403523Notes

Reaction equation

HRID 403523 reaction equation
[NH2:1][C:2]1[C:7]([N:8]([CH3:13])[C:9](=O)[O:10]C)=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[CH:19]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][N:24]=3)[N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:16]=2)[N:3]=1.[H-].[Na+]>CN(C=O)C.O.CCOCC>[NH2:1][C:2]1[N:3]=[C:4]([C:15]2[CH:19]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][N:24]=3)[N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:16]=2)[N:5]=[C:6]2[C:7]=1[N:8]([CH3:13])[C:9](=[O:10])[NH:14]2

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 68109065HCID 68109065, compound

Product 1

HCID 56598119HCID 56598119, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-5-(oxazol-2-yl)-1H-pyrazol-3-yl)pyrimidin-5-yl(methyl)carbamate (82 mg, 0.19 mmol) in DMF (3.7 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 15 mg, 0.37 mmol). The solution was immediately warmed to ambient temperature and stirred for 45 min. Water (3 mL) was added, and after stirring for 5 minutes, the crude reaction mixture was diluted with ethyl acetete (100 mL) and water (75 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×50 mL). The organics were combined, washed with water (2×50 mL) and brine (50 mL), dried over magnesium sulfate, and filtered. The solvent was removed in vacuo to give the crude product as an orange solid. The crude material was brought up in ether (10 mL) and the orange solid was filtered off. The procedure was repeated to give 6-amino-2-(1-(2-fluorobenzyl)-5-(oxazol-2-yl)-1H-pyrazol-3-yl)-7-methyl-7H-purin-8(9H)-one (51 mg, 0.13 mmol, 67% yield) as a pink solid. 1H NMR (400 MHz, DMSO): δ 11.57 (s, 1H), 8.31 (s, 1H), 7.41 (s, 1H), 7.35-7.31 (m, 2H), 7.25-7.20 (m, 1H), 7.12 (t, 1H), 6.96-6.93 (m, 1H), 6.65 (s, 2H), 6.01 (s, 2H), 3.45 (s, 3H).

Workup

  1. stirringafter stirring for 5 minutes
  2. customthe crude reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washwashed with water (2×50 mL) and brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customto give the crude product as an orange solid
  10. filtrationthe orange solid was filtered off

Sources & evidence

ORD record
ord-39cb4c996b3248a8b7a18b8da3fcf821
Source dataset
uspto-grants-2014_06
Patent number
US08748442B2

Reaction notes

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