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Triethylamine → (S)-4-(2-chloro-6-neopentyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

HRID 1626540
Notes
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Reaction equation

HRID 1626540 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1.[CH3:19][C:20]([CH:23]=O)([CH3:22])[CH3:21].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(OCC)(=O)C.O>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][N:10]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:9][C:7]=2[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86663150(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride2×

Product 1

HCID 86663152(S)-4-(2-chloro-6-neopentyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride (intermediate 6) (163 mg, 0.56 mmol) was stirred in THF (2 mL) with pivaldehyde (0.124 mL, 1.12 mmol) and triethylamine (0.234 mL, 1.68 mmol). After 1 h sodium triacetoxyborohydride (237 mg, 1.12 mmol) was added and the reaction was stirred overnight. Water and ethyl acetate were added. The organic layer was washed (brine) and concentrated in vacuo to give an orange oil, which was used crude.

Workup

  1. washThe organic layer was washed (brine)
  2. concentrationconcentrated in vacuo
  3. customto give an orange oil, which

Sources & evidence

ORD record
ord-04a6db200b324f7993a9a0b6abf11c14
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes