Formaldehyde → HCID 58362520, compound

HRID 2361523Notes

Reaction equation

HRID 2361523 reaction equation
[N:1]1[C:2]2[N:3]([C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:4]=[CH:5][C:6]=1[C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([F:14])[CH:8]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:26](C)=O.[Na+]>ClCCCl>[N:1]1[C:2]2[N:3]([C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:4]=[CH:5][C:6]=1[C:7]1[CH:13]=[CH:12][C:10]([NH:11][CH3:26])=[C:9]([F:14])[CH:8]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58362372HCID 58362372, compound

Product 1

HCID 58362520HCID 58362520, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-2-fluoroaniline (20 mg, 0.072 mmol) in 1 mL DCE was added paraformaldehyde (4.5 mg, 0.14 mmol), followed by NaBH(AcO)3 (51 mg, 0.24 mmol). The reaction was stirred at rt for 6 h and quenched by adding Na2CO3 (5 mL, saturated). The mixture was extracted with EtOAc (2×10 mL) and the combined organic phase was washed with water (2×20 mL) and concentrated under reduced pressure. The residue was subjected to reversed phase HPLC (TFA buffered water/MeCN) to afford 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-2-fluoro-N-methylaniline as orange solid (4.5 mg, 21%). 1H NMR (400 MHz, methanol-d4): δ 9.10 (d, J=7.2 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H), 8.01 (d, J=11.2 Hz, 2H), 7.75 (d, J=8.4 Hz, 1H), 7.56 (d, J=7.6 Hz, 1H), 7.51 (t, J=7.2 Hz, 1H), 7.38 (d, J=7.2 Hz, 1H), 6.94 (t, J=8.8 Hz, 1H), 2.90 (s, 3H); MS (ESI) m/z [M+H]+293.

Workup

  1. customquenched
  2. additionby adding Na2CO3 (5 mL, saturated)
  3. extractionThe mixture was extracted with EtOAc (2×10 mL)
  4. washthe combined organic phase was washed with water (2×20 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71051097d1e94ca4bea2d0b754f8015c
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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