Formaldehyde → HCID 16062913, compound

HRID 1917256Notes

Reaction equation

HRID 1917256 reaction equation
[CH:1]1([C:6]2[N:7]=[C:8]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:9]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:10]=3[N:16]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:28](C)=O.[Na+]>CO.[OH-].[Na+]>[CH:1]1([C:6]2[N:7]=[C:8]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:9]3[CH2:15][CH2:14][N:13]([CH3:28])[CH2:12][CH2:11][C:10]=3[N:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 16062781HCID 16062781, compound

Product 1

HCID 16062913HCID 16062913, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-cyclopentyl-4-(4-fluoro-phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine (0.035 g, 0.112 mmol) in MeOH (1 mL) was added formaldehyde (37% in water; 0.10 mL) and NaBH(OAc)3 (0.032 g, 0.151 mmol). After the reaction was judged complete, the mixture was diluted with 1 N NaOH and extracted with CH2Cl2 (3×). The combined organic layers were dried and concentrated. The resulting residue was purified via SiO2 chromatography (1-7% 2 M NH3 in MeOH/CH2Cl2) to give 0.031 g (87%) of the title compound. MS (ESI): exact mass calcd. for C20H24FN3, 325.20; m/z found, 326.4 [M+H]+. 1H NMR (CDCl3): 7.47 (dd, J=5.4, 8.8, 2H), 7.15 (t, J=8.7, 2H), 3.38-3.30 (m, 1H), 3.20 (dd, J=4.1, 6.3, 2H), 2.97 (dd, J=4.2, 5.9, 2H), 2.71-2.70 (m, 2H), 2.60 (m, 2H), 2.41 (s, 3H), 2.12-2.05 (m, 2H), 1.99-1.91 (m, 2H), 1.87-1.79 (m, 2H), 1.73-1.63 (m, 2H).

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe resulting residue was purified via SiO2 chromatography (1-7% 2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3311ff941bb84e2abc92afaabbc8b363
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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