Hydrochloric Acid → Diethyl-[4-(4-fluoro-phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-c]azepin-2-yl]-amine

HRID 72796Notes

Reaction equation

HRID 72796 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C:11]2[C:15]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[N:16][C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[N:18][C:10]=2[CH2:9]1)=O)(C)(C)C.Cl>CCOC(C)=O.O1CCOCC1>[CH2:22]([N:19]([CH2:20][CH3:21])[C:17]1[N:16]=[C:15]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][C:10]=2[N:18]=1)[CH3:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67369370HCID 67369370, compound

Product 1

HCID 46205216Diethyl-[4-(4-fluoro-phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-c]azepin-2-yl]-amineYield 90%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-diethylamino-4-(4-fluoro-phenyl)-5,6,7,9-tetrahydro-pyrimido[4,5-c]azepine-8-carboxylic acid tert-butyl ester (0.058 g, 0.14 mmol) in EtOAc (1 mL) was added 4 M HCl in dioxane (2 mL). After 16 h, the mixture was concentrated, diluted with saturated (satd.) aqueous (aq.) NaHCO3, and extracted with CH2Cl2. The combined organic layers were dried and concentrated. Purification by FCC (2 M NH3 in MeOH/CH2Cl2) provided the title compound (>90%). HPLC: Rt=9.7 min. MS (ESI): mass calcd. for C18H23FN4, 314.4; m/z found, 315.4 [M+H]+. 1H NMR (CDCl3): 7.47 (dd, J=8.7, 5.5, 2H), 7.11 (t, J=8.7, 2H), 3.96 (5, 2H), 3.64 (q, J=7.0, 4H), 3.21-3.18 (m, 1H), 2.80-2.76 (m, 2H), 1.93-1.86 (m, 2H), 1.71-1.67 (m, 1H), 1.17 (t, J=7.0, 6H).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with saturated (satd.) aqueous (aq.) NaHCO3
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customPurification by FCC (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6c17690f28564c4093fdae5dd8852028
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

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