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Hydrochloric Acid → HCID 19894561, compound

HRID 893019
Notes
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Reaction equation

HRID 893019 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:9]=[C:8]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:24]([C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:35]=1[OH:36])[CH:31]=O)([CH3:27])([CH3:26])[CH3:25].C([BH3-])#N.[Na+]>CO>[CH3:40][C:37]([C:34]1[CH:33]=[C:30]([CH2:31][N:15]2[CH2:16][CH2:17][N:12]([C:10]3[CH:9]=[C:8]([N:18]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[N:7]=[C:6]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[N:11]=3)[CH2:13][CH2:14]2)[CH:29]=[C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:35]=1[OH:36])([CH3:38])[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine

Product 1

HCID 19894561HCID 19894561, compound

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

2,6-bis(1-pyrrolidinyl)-4-(1-piperazinyl)pyrimidine (PREPARATION A-22) is stirred in methanol (10 ml). To the above solution is added saturated ethereal hydrochloric acid until the solution clarifies. To this mixture is added 3,5-di-t-butyl-4-hydroxybenzaldehyde and the mixture stirred for 30 min at which time sodium cyanoborohydride is added in two batches. The mixture is stirred at 20°-25° for 18 hr and quenched with hydrochoric acid (10%, 25 ml) added dropwise at 0°. The methanol is removed under a stream of nitrogen and the acidic mixture is extracted with ethyl acetate (25 ml). The aqueous phase is then made basic with hydroxide (45%) at 0°. The aqueous basic phase is then extracted with methylene chloride (2×). The organic phases are combined and dried over sodium sulfate, following which the mixture is concentrated under at reduced pressure. The concentrate is flashed chromatographed on silica gel eluting with hexane/ethyl acetate (1/1) or ethyl acetate. The appropriate fractions are pooled and concentrated to give the title compound.

Workup

  1. additionis added in two batches
  2. customquenched with hydrochoric acid (10%, 25 ml)
  3. additionadded dropwise at 0°
  4. customThe methanol is removed under a stream of nitrogen
  5. extractionthe acidic mixture is extracted with ethyl acetate (25 ml)
  6. customis then made basic with hydroxide (45%) at 0°
  7. extractionThe aqueous basic phase is then extracted with methylene chloride (2×)
  8. dry with materialdried over sodium sulfate
  9. concentrationis concentrated under at reduced pressure
  10. customThe concentrate is flashed chromatographed on silica gel eluting with hexane/ethyl acetate (1/1) or ethyl acetate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6cb9d359f5194cf3a40c0500db368100
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05120843

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes