Trimethyl orthoformate → HCID 86623545, compound

HRID 391032Notes

Reaction equation

HRID 391032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[N:17]=[C:18]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:19]2[S:24][C:23]([CH:25]=O)=[CH:22][C:20]=2[N:21]=1.COC(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:15][C:16]1[N:17]=[C:18]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[C:19]2[S:24][C:23]([CH2:25][N:11]3[CH2:10][CH2:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)([OH:14])[CH2:13][CH2:12]3)=[CH:22][C:20]=2[N:21]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 86623545HCID 86623545, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To 4-(4-chlorophenyl)-4-hydroxypiperidine (368 mg, 1.74 mmol) in dichloroethane was added 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 from Example 3 (400 mg, 1.41 mmol) and trimethylorthoformate. After stirring for 1 hour at room temperature, sodium triacetoxyborohydride was added and the reaction mixture stirred overnight. The mixture was quenched with saturated aqueous Na2CO3. Chloroform/brine extraction gave crude material which was then triturated with hot ethyl acetate to give 1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-4-(4-chloro-phenyl)-piperidin-4-ol. (272 mg, 0.56 mmol).

Workup

  1. stirringthe reaction mixture stirred overnight
  2. customThe mixture was quenched with saturated aqueous Na2CO3
  3. extractionChloroform/brine extraction
  4. customgave crude material which
  5. customwas then triturated with hot ethyl acetate

Sources & evidence

ORD record
ord-18cc552f5407477685c04f3fe1e94d97
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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